Aromatic amine derivative, and organic electroluminescent element

ABSTRACT

Provided is an organic electroluminescence device that provides high efficiency and a long lifetime. The device includes an aromatic amine including at least one substituent A having dibenzofuran and at least one substituent B selected from groups having dibenzofuran or carbazole. The substituent A and the substituent B include groups different from each other and are bonded to the same or different nitrogen atoms in the molecule. The molecules of the aromatic amine hardly crystallize, improving yield in producing the organic electroluminescence device. The device includes an organic thin film layer formed of one or more layers including at least a light emitting layer, the organic thin film layer being interposed between a cathode and an anode. The aromatic amine is contained in at least one layer, particularly a hole transport layer, in the organic thin film layer.

This application is a continuation of U.S. patent application Ser. No.12/998,732, filed Aug. 5, 2011, now U.S. Pat. No. 8,614,010, which is aNational Phase (371) filing of PCT/JP2009/069808, filed Nov. 24, 2009.

TECHNICAL FIELD

The present invention relates to an aromatic amine derivative and anorganic electroluminescence (organic EL) device using the same, and moreparticularly, to an aromatic amine derivative capable of providing highefficiency even at high temperatures and increasing a lifetime of theorganic EL device by using an aromatic amine derivative having aspecific structure as a hole transporting material.

BACKGROUND ART

An organic EL device is a spontaneous light emitting device whichutilizes such a principle that a fluorescent substance emits light byvirtue of recombination energy of holes injected from an anode andelectrons injected from a cathode by an application of an electricfield. Since an organic EL device of the laminate type capable of beingdriven under low electric voltage has been reported by C. W. Tang et al.of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied PhysicsLetters, Volume 51, Page 913, 1987, or the like), many studies have beenconducted for an organic EL device using an organic material as aconstituent material. Tang et al. used tris(8-quinolinolato) aluminumfor a light emitting layer and a triphenyldiamine derivative for a holetransporting layer. Advantages of the laminate structure reside in thefollowings: an efficiency of the hole injection into the light emittinglayer can be increased; an efficiency of forming excitons which areformed by blocking and recombining electrons injected from the cathodecan be increased; and excitons formed within the light emitting layercan be enclosed. As described above, for the device structure of theorganic EL device, a two-layered structure having a hole transporting(injecting) layer and an electron transporting light emitting layer anda three-layered structure having a hole transporting (injecting) layer,a light emitting layer, an electron transporting (injecting) layer, andthe like are widely known. In order to increase the efficiency ofrecombination of injected holes and electrons in such devices of thelaminate type, the device structure and the process of forming thedevice have been studied.

In general, when an organic EL device is driven or stored in anenvironment of high temperature, there occur adverse affects such as achange in luminescent color, a decrease in emission efficiency, anincrease in driving voltage, and a decrease in a lifetime of lightemission. In order to prevent the adverse affects, it has been necessarythat the glass transition temperature (Tg) of the hole transportingmaterial be elevated. Therefore, it is necessary that many aromaticgroups be held within a molecule of the hole transporting material (forexample, an aromatic diamine derivative of Patent Literature 1 and anaromatic fused ring diamine derivative of Patent Literature 2), and ingeneral, a structure having 8 to 12 benzene rings is preferably used.

However, in the case of a highly symmetrical compound and a compoundhigh in flatness each having a large number of aromatic groups in amolecule, crystallization is liable to occur upon production of theorganic EL device through the formation of a thin film by using thosehole transporting materials. As a result, there arises a problem such asclogging of an outlet of a crucible to be used in vapor deposition or areduction in yields of the organic EL device due to generation ofdefects of the thin film resulting from the crystallization. Inaddition, a compound having a large number of aromatic groups in any oneof its molecules generally has a high glass transition temperature (Tg),but has a high sublimation temperature. Accordingly, there arises aproblem in that the lifetime of the compound is short probably because aphenomenon such as decomposition at the time of the vapor deposition orthe formation of a nonuniform deposition film occurs.

Meanwhile, Patent Literatures 3 to 5 report amine compounds each havingdibenzofuran. However, those compounds are each of a structure havingdibenzofuran in the central skeleton of a diamine compound. PatentLiteratures 6 to 9 report compounds each having dibenzofuran bonded to amonoamine through an aryl group. However, none of the compounds providessufficient performance when used in an organic EL device.

In addition, a large number of reports have been made on amine compoundsin each of which N-carbazole is bonded to an amine through an arylgroup. Examples of the reports include Patent Literatures 10 to 12.However, none of the compounds provides sufficient performance when usedin an organic EL device.

Further, Patent Literatures 13 and 14 report amine compounds in each ofwhich 3-carbazole is directly bonded to an amine. However, none of thecompounds provides sufficient performance when used in an organic ELdevice. In addition, Patent Literatures 15 and 16 report amine compoundsin each of which 3-carbazole is bonded to an amine through an arylgroup. However, none of the compounds provides sufficient performancewhen used in an organic EL device.

As described above, high-efficiency, long-lifetime organic EL deviceshave been reported, but none of them provides sufficient performance,and hence the development of an organic EL device having additionallyexcellent performance has been strongly desired.

CITATION LIST Patent Literature

[PTL 1] U.S. Pat. No. 4,720,432 A

[PTL 2] U.S. Pat. No. 5,061,569 A

[PTL 3] JP 2005-112765 A

[PTL 4] JP 11-111460 A

[PTL 5] WO 2006/122630 A1

[PTL 6] WO 2006/128800 A1

[PTL 7] JP 2006-151844 A

[PTL 8] JP 2008-021687 A

[PTL 9] WO 2007/125714 A1

[PTL 10] U.S. Pat. No. 6,242,115 A

[PTL 11] JP 2007-284431 A

[PTL 12] JP 2003-031371 A

[PTL 13] JP 2007-318101 A

[PTL 14] JP 2006-151979 A

[PTL 15] JP 2005-290000 A

[PTL 16] WO 2008/062636 A1

SUMMARY OF INVENTION Technical Problem

The present invention has been made to solve the problems, and an objectof the present invention is to provide an organic electroluminescencedevice that not only provides high efficiency even at high temperaturesbut also has a long lifetime, and an aromatic amine derivative thatrealizes the device.

Solution to Problem

The inventors of the present invention have made extensive studies toachieve the object. As a result, the inventors have found that the useof a novel aromatic amine derivative having two kinds of specificsubstituents as a material for an organic EL device, in particular, ahole injecting material or a hole transporting material can solve theproblems.

The following facts have been found. The specific substituents aresuitably a group having a dibenzofuran structure and a group having adibenzofuran structure or a carbazole structure. The molecular symmetryof an amine derivative having at least one group having a dibenzofuranstructure and at least one group having a dibenzofuran structure and/ora carbazole structure, the groups being different from each other, canbe reduced. Accordingly, the derivative shows a small intermolecularinteraction, crystallizes to a reduced extent, and can improve the yieldin the production of an organic EL device. In addition, theabove-mentioned amine derivative improves efficiency because thederivative has so large an Eg as to be capable of effectively blockingelectrons from a light emitting layer. In addition, the derivative has alifetime-lengthening effect because the derivative suppresses theinjection of electrons into a hole transporting layer. In particular, acombination of the derivative and a blue light emitting device exerts asignificant lifetime-lengthening effect. The inventors of the presentinvention have completed the present invention on the basis of thosefindings.

That is, the present invention provides the following.

1. An aromatic amine derivative, including at least one substituent Arepresented by the following general formula (1) and at least onesubstituent B represented by the following general formula (2) or (3) ina molecule thereof, in which: the substituent A and the substituent Binclude groups different from each other; and the substituent A and thesubstituent B are bonded to the same nitrogen atom, or differentnitrogen atoms, in the molecule:

[in the formula

L¹ and L² each independently represent a single bond, or a substitutedor unsubstituted arylene group having 6 to 50 ring carbon atoms, and L³represents a substituted or unsubstituted arylene group having 6 to 50ring carbon atoms, provided that a substituent which any one of L¹ to L³may have includes a linear or branched alkyl group having 1 to 10 carbonatoms, a cycloalkyl group having 3 to 10 ring carbon atoms, atrialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl grouphaving 18 to 30 ring carbon atoms, an alkylarylsilyl group having 8 to15 carbon atoms whose aryl portion has 6 to 14 ring carbon atoms, anaryl group having 6 to 14 ring carbon atoms, a halogen atom, or a cyanogroup;

X represents an oxygen atom or a —N(Ar¹)— group;

Ar¹ represents a substituted or unsubstituted aryl group having 6 to 14ring carbon atoms, and a substituent which Ar¹ may have includes alinear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkylgroup having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3to 10 carbon atoms, a triarylsilyl group having 18 to 30 ring carbonatoms, an alkylarylsilyl group having 8 to 15 carbon atoms whose arylportion has 6 to 14 ring carbon atoms, an aryl group having 6 to 14 ringcarbon atoms, a halogen atom, or a cyano group;

a, c, e, and f each independently represent an integer of 0 to 4;

b and d each independently represent an integer of 0 to 3; and

R¹ to R⁶ each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 14 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R¹'s to R⁶'s adjacent to eachother may be bonded to each other to form a saturated or unsaturated,divalent group that forms a ring,

provided that hydrogen atoms in the aromatic amine derivative includedeuterium atoms].

2. The aromatic amine derivative according to the above-mentioned item1, in which when the X in the general formula (2) represents a —N(Ar¹)—group, the L² is represented by the following general formula (4):

[in the formula:

R⁷ and R⁸ each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 16 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R⁷'s and R⁸'s adjacent toeach other may be bonded to each other to form a saturated orunsaturated ring; and

g and h each independently represent an integer of 0 to 4].

3. The aromatic amine derivative according to the above-mentioned item1, in which the substituent B is represented by the general formula (3).

4. The aromatic amine derivative according to the above-mentioned item1, in which when the L³ in the general formula (3) is represented by thefollowing general formula (4):

[in the formula:

R⁷ and R⁸ each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 16 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R⁷'s and R⁸'s adjacent toeach other may be bonded to each other to form a saturated orunsaturated ring; and

g and h each independently represent an integer of 0 to 4].

5. The aromatic amine derivative according to the above-mentioned item1, in which the substituent A is represented by the following generalformula (1) and the substituent B is represented by the followinggeneral formula (2-1) or (3):

[in the formula:

L¹ and L² each independently represent a single bond, or a substitutedor unsubstituted arylene group having 6 to 50 ring carbon atoms, and L³represents a substituted or unsubstituted arylene group having 6 to 50ring carbon atoms, provided that a substituent which any one of L¹ to L³may have includes a linear or branched alkyl group having 1 to 10 carbonatoms, a cycloalkyl group having 3 to 10 ring carbon atoms, atrialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl grouphaving 18 to 30 ring carbon atoms, an alkylarylsilyl group having 8 to15 carbon atoms whose aryl portion has 6 to 14 ring carbon atoms, anaryl group having 6 to 14 ring carbon atoms, a halogen atom, or a cyanogroup;

Ar¹ represents a substituted or unsubstituted aryl group having 6 to 14ring carbon atoms, and a substituent which Ar¹ may have includes alinear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkylgroup having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3to 10 carbon atoms, a triarylsilyl group having 18 to 30 ring carbonatoms, an alkylarylsilyl group having 8 to 15 carbon atoms whose arylportion has 6 to 14 ring carbon atoms, an aryl group having 6 to 14 ringcarbon atoms, a halogen atom, or a cyano group;

a, c, e, and f each independently represent an integer of 0 to 4;

b and d each independently represent an integer of 0 to 3; and

R¹ to R⁶ each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 14 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R¹'s to R⁶'s adjacent to eachother may be bonded to each other to form a saturated or unsaturated,divalent group that forms a ring].

6. The aromatic amine derivative according to the above-mentioned item5, in which the substituent A is represented by the following generalformula (1-1) or (1-2).

7. The aromatic amine derivative according to the above-mentioned item1, in which the substituent A and the substituent B are eachindependently represented by the following general formula (1):

[in the formula:

L¹ represents a single bond, or a substituted or unsubstituted arylenegroup having 6 to 50 ring carbon atoms, and a substituent which L¹ mayhave includes a linear or branched alkyl group having 1 to 10 carbonatoms, a cycloalkyl group having 3 to 10 ring carbon atoms, atrialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl grouphaving 18 to 30 ring carbon atoms, an alkylarylsilyl group having 8 to15 carbon atoms whose aryl portion has 6 to 14 ring carbon atoms, anaryl group having 6 to 14 ring carbon atoms, a halogen atom, or a cyanogroup;

a represents an integer of 0 to 4;

b represents an integer of 0 to 3; and

R¹ and R² each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 14 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R¹'s and R²'s adjacent toeach other may be bonded to each other to form a saturated orunsaturated, divalent group that forms a ring].

8. The aromatic amine derivative according to the above-mentioned item7, in which the substituent A and the substituent B are eachindependently represented by any one of the following general formulae(1-1) to (1-3).

9. The aromatic amine derivative according to the above-mentioned item8, in which the substituent A is represented by the general formula(1-1) and the substituent B is represented by the general formula (1-2).10. The aromatic amine derivative according to the above-mentioned item1, further including at least one terphenyl group.

11. The aromatic amine derivative according to the above-mentioned item1, in which the aromatic amine derivative is represented by any one ofthe following general formulae (5) to (9):

{in the formulae:

at least one of Ar² to Ar⁴ represents the substituent A represented bythe general formula (1), at least one of Ar² to Ar⁴ represents thesubstituent B represented by the general formula (2) or (3), and thesubstituent A and the substituent B include groups different from eachother;

at least one of Ar⁵ to Ar⁸ represents the substituent A represented bythe general formula (1), at least one of Ar⁵ to Ar⁸ represents thesubstituent B represented by the general formula (2) or (3), and thesubstituent A and the substituent B include groups different from eachother;

at least one of Ar⁹ to Ar¹³ represents the substituent A represented bythe general formula (1), at least one of Ar⁹ to Ar¹³ represents thesubstituent B represented by the general formula (2) or (3), and thesubstituent A and the substituent B include groups different from eachother;

at least one of Ar¹⁴ to Ar¹⁹ represents the substituent A represented bythe general formula (1), at least one of Ar¹⁴ to Ar¹⁹ represents thesubstituent B represented by the general formula (2) or (3), and thesubstituent A and the substituent B include groups different from eachother;

at least one of Ar²⁰ to Ar²⁵ represents the substituent A represented bythe general formula (1), at least one of Ar²⁰ to Ar²⁵ represents thesubstituent B represented by the general formula (2) or (3), and thesubstituent A and the substituent B include groups different from eachother;

groups out of Ar² to Ar²⁵ except the substituent A and the substituent Beach independently include a substituted or unsubstituted aryl grouphaving 6 to 50 ring carbon atoms;

L⁴ to L¹² each independently represent a substituted or unsubstitutedarylene group having 6 to 50 ring carbon atoms; and

substituents which Ar² to Ar²⁵ and L⁴ to L¹² may have each independentlyinclude a linear or branched alkyl group having 1 to 10 carbon atoms, acycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl grouphaving 3 to 10 carbon atoms, a triaryl silyl group having 18 to 30 ringcarbon atoms, an alkylarylsilyl group having 8 to 15 carbon atoms whosearyl portion has 6 to 14 ring carbon atoms, an aryl group having 6 to 14ring carbon atoms, a halogen atom, or a cyano group.

12. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative is represented by the generalformula (5).

13. The aromatic amine derivative according to the above-mentioned item11, in which the L¹ to L¹² each independently represent a phenylenegroup, a naphthylene group, a biphenylene group, a terphenylene group, afluorenylene group, or a 9,9-dimethylfluorenylene group.14. The aromatic amine derivative according to the above-mentioned item11, in which the L¹ to L¹² are each independently represented by any oneof the following general formulae (4), (10), and (11):

[in the formulae:

R⁷ to R¹¹ each independently represent a linear or branched alkyl grouphaving 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ringcarbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 16 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R⁷'s to R¹¹'s adjacent toeach other may be bonded to each other to form a saturated orunsaturated ring;

R¹² and R¹³ each independently represent a linear or branched alkylgroup having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10ring carbon atoms;

g, h, and i each independently represent an integer of 0 to 4; and

j and k each independently represent an integer of 0 to 3].

15. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² isrepresented by the general formula (1), and the Ar³ and the Ar⁴ are eachindependently represented by the general formula (3) or (2-1).

16. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² andthe Ar³ are each represented by the general formula (1), and the Ar⁴ isrepresented by the general formula (3) or (2-1).17. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² isrepresented by the general formula (1), the Ar³ is represented by thegeneral formula (3) or (2-1), and the Ar⁴ represents a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms [provided thatsubstituents of the Ar⁴ each independently include any one of an arylgroup having 6 to 50 ring carbon atoms, a branched or linear alkyl grouphaving 1 to 50 carbon atoms, a halogen atom, and a cyano group].18. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (6) in which the Ar⁵ andthe Ar⁶ are each represented by the general formula (1), and the Ar⁷ andthe Ar⁸ are each independently represented by the general formula (3) or(2-1).19. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (6) in which the Ar⁵ andthe Ar⁷ are each represented by the general formula (1), and the Ar⁶ andthe Ar⁸ are each independently represented by the general formula (3) or(2-1).20. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (7) in which the Ar⁹ isrepresented by the general formula (1), and the Ar¹¹ and the Ar¹² areeach independently represented by the general formula (3) or (2-1).21. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (7) in which the Ar¹¹ andthe Ar¹² are each represented by the general formula (1), and the Ar⁹ isrepresented by the general formula (3) or (2-1).22. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (8) in which the Ar¹⁴ andthe Ar¹⁹ are each represented by the general formula (1), and the Ar¹⁶and the Ar¹⁷ are each independently represented by the general formula(3) or (1).23. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (8) in which the Ar¹⁶ andthe Ar¹⁷ are each represented by the general formula (1), and the Ar¹⁴and the Ar¹⁹ are each independently represented by the general formula(3) or (2-1).24. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (9) in which the Ar²⁰, theAr²², and the Ar²⁴ are each represented by the general formula (1), andthe Ar²¹, the Ar²³, and the Ar²⁵ are each independently represented bythe general formula (3) or (2-1).

25. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² toAr⁴ are each represented by the general formula (1-2).

26. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² toAr⁴ are each represented by the general formula (1-1).27. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which two of theAr² to Ar⁴ are each represented by the general formula (1-2), and one ofthe Ar² to Ar⁴ represents a substituted or unsubstituted aryl grouphaving 6 to 16 ring carbon atoms.28. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which two of theAr² to Ar⁴ are each represented by the general formula (1-1), and one ofthe Ar² to Ar⁴ represents a substituted or unsubstituted aryl grouphaving 6 to 16 ring carbon atoms.29. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which at least oneof the Ar² to Ar⁴ is represented by the general formula (1-2), and atleast one of the Ar² to Ar⁴ is represented by the general formula (1-1).30. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² isrepresented by the general formula (1-2), and the Ar³ and the Ar⁴ areeach independently represented by the general formula (1).31. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar² andthe Ar³ are each represented by the general formula (1-2), and the Ar⁴is represented by the general formula (1-1).

32. The aromatic amine derivative according to the above-mentioned item11, in which at least two of the Ar⁵ to Ar⁸ are each, at least two ofthe Ar⁹ to Ar¹³ are each, at least one of the Ar¹⁴ to Ar¹⁹ is, or atleast one of the Ar²⁰ to Ar²⁵ is represented by the general formula(1-2) or (1-1).

33. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes any one of anaromatic amine derivative represented by the general formula (6) inwhich at least one of the Ar⁵ to Ar⁸ is represented by the generalformula (1-2) and at least one of the Ar⁵ to Ar⁸ except the at least onerepresented by the general formula (1-2) is represented by the generalformula (1-1), an aromatic amine derivative represented by the generalformula (7) in which at least one of the Ar⁹ to Ar¹³ is represented bythe general formula (1-2) and at least one of the Ar⁹ to Ar¹³ except theat least one represented by the general formula (1-2) is represented bythe general formula (1-1), an aromatic amine derivative represented bythe general formula (8) in which at least one of the Ar¹⁴ to Ar¹⁹ isrepresented by the general formula (1-2) and at least one of the Ar¹⁴ toAr¹⁹ except the at least one represented by the general formula (1-2) isrepresented by the general formula (1-1), and an aromatic aminederivative, represented by the general formula (9) in which at least oneof the Ar²⁰ to Ar²⁵ is represented by the general formula (1-2) and atleast one of the Ar²⁰ to Ar²⁵ except the at least one represented by thegeneral formula (1-2) is represented by the general formula (1-1).34. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar⁵ isrepresented by the general formula (1-2) and the Ar⁶ is represented bythe general formula (1-1).35. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (5) in which the Ar⁵ andthe Ar⁷ are each represented by the general formula (1-2) and the Ar⁶and the Ar⁸ are each represented by the general formula (1-1).36. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (6) in which the Ar⁹ isrepresented by the general formula (1-2) and the Ar¹¹ and the Ar¹² areeach represented by the general formula (1-1).37. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (6) in which the Ar¹⁰ andthe Ar¹³ are each represented by the general formula (1-2) and the Ar¹¹and the Ar¹² are each represented by the general formula (1-1).38. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (8) in which the Ar¹⁴ andthe Ar¹⁹ are each represented by the general formula (1-2) and the Ar¹⁶and the Ar¹⁷ are each represented by the general formula (1-1).39. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (8) in which the Ar¹⁵ andthe Ar¹⁸ are each represented by the general formula (1-2) and the Ar¹⁶and the Ar¹⁷ are each represented by the general formula (1-1).40. The aromatic amine derivative according to the above-mentioned item11, in which the aromatic amine derivative includes an aromatic aminederivative represented by the general formula (9) in which the Ar²⁰, theAr²², and the Ar²⁴ are each represented by the general formula (1-2) andthe Ar²¹, the Ar²³, and the Ar²⁵ are each represented by the generalformula (1-1).41. The aromatic amine derivative according to the above-mentioned item11, in which groups out of the Ar² to Ar²⁵ except the substituent A andthe substituent B each independently include a phenyl group, a naphthylgroup, a biphenyl group, a terphenyl group, or a fluorenyl group.

42. The aromatic amine derivative according to the above-mentioned item1, in which the aromatic amine derivative is used as a material for anorganic electroluminescence device.

43. The aromatic amine derivative according to the above-mentioned item1, in which the aromatic amine derivative is used as a hole transportingmaterial for an organic electroluminescence device.

44. An organic electroluminescence device, including an organic thinfilm layer formed of one or more layers including at least a lightemitting layer, the organic thin film layer being interposed between acathode and an anode, in which at least one layer of the organic thinfilm layer contains the aromatic amine derivative according to theabove-mentioned item 1.45. The organic electroluminescence device according to theabove-mentioned item 1, in which: the organic thin film layer has a holetransporting layer and/or a hole injecting layer; and the aromatic aminederivative according to the above-mentioned item 44 is incorporated intothe hole transporting layer and/or the hole injecting layer.46. The organic electroluminescence device according to theabove-mentioned item 44, in which: the organic thin film layer has ahole transporting zone including at least a hole transporting layer anda hole injecting layer; and the aromatic amine derivative according tothe above-mentioned item 1 is incorporated into a layer out of directcontact with the light emitting layer in the hole transporting zone.47. The organic electroluminescence device according to theabove-mentioned item 44, in which the aromatic amine derivativeaccording to any one of the above-mentioned items 1 to 41 isincorporated as a main component into the hole transporting layer and/orthe hole injecting layer.48. The organic electroluminescence device according to theabove-mentioned item 44, in which the light emitting layer contains astyrylamine compound and/or an arylamine compound.49. The organic electroluminescence device according to theabove-mentioned item 44, in which a layer in contact with the anode outof layers for forming the hole injecting layer and/or the holetransporting layer includes a layer containing an acceptor material.50. The organic electroluminescence device according to theabove-mentioned item 44, in which the organic electroluminescence deviceemits blue light.

Advantageous Effects of Invention

The aromatic amine derivative of the present invention hardlycrystallizes, and the use of the derivative as a material for an organicEL device provides a device that not only provides high efficiency evenat high temperatures but also has a long lifetime.

DESCRIPTION OF EMBODIMENTS

The aromatic amine derivative of the present invention is a compoundhaving at least one substituent A represented by the general formula (1)and at least one substituent B represented by the general formula (2) or(3) in any one of its molecules, in which: the substituent A and thesubstituent B are groups different from each other; and the substituentA and the substituent B are bonded to the same nitrogen atom, ordifferent nitrogen atoms, in the molecule.

The “aromatic amine derivative” in the present invention is preferablyan amine compound having a molecular weight of 300 to 2,000 and having asubstituent formed of an aromatic compound. The molecular weight is morepreferably 400 to 1,500, particularly preferably 500 to 1,200. When themolecular weight is 300 to 2,000, the compound can be purified bysublimation, and as a result, the purity of the compound can beimproved. The use of the compound improves the performance of a deviceto be obtained. In addition, the case where the molecular weight is 300to 2,000 is preferred because the device can be produced by a depositionmethod.

The “aromatic amine derivative”, which is not particularly limited, isrepresented by preferably any one of the general formulae (5) to (9),more preferably the general formula (5) or (6), particularly preferablythe general formula (5). A monoamine derivative represented by thegeneral formula (5) and a diamine derivative represented by the generalformula (6) can be expected to be produced at low costs because thederivatives can each be synthesized with relative ease. In addition, themonoamine derivative and the diamine derivative each have a largeionization potential (which may hereinafter be abbreviated as “IP”).Accordingly, when any such derivative is used as a hole transportingmaterial, the property by which holes are injected into a light emittinglayer is improved, and hence a reduction in the voltage at which thedevice is driven can be expected. In particular, an improvement in theluminous efficiency, and the lengthening of the lifetime, of the devicecan be expected from the monoamine derivative because the derivative hasso large an energy gap as to be capable of suppressing the injection ofelectrons into a hole transporting layer.

In the general formulae (1) to (3), (1-1) to (1-3), and (2-1), R¹ to R⁶each independently represent a linear or branched alkyl group having 1to 10, preferably 1 to 6, carbon atoms, a cycloalkyl group having 3 to10, preferably 5 to 7, ring carbon atoms, a trialkylsilyl group having 3to 10, preferably 3 to 6, carbon atoms, a triarylsilyl group having 18to 30, preferably 18 to 24, ring carbon atoms, an alkylarylsilyl grouphaving 8 to 15, preferably 8 to 12, carbon atoms (its aryl portion has 6to 14, preferably 6 to 10, ring carbon atoms), an aryl group having 6 to16, preferably 6 to 10, ring carbon atoms, a halogen atom (a fluorineatom is preferred), or a cyano group, and a plurality of R¹'s to R⁶'sadjacent to each other may be bonded to themselves, or R¹ and R², R³ andR⁴, or R⁵ and R⁶ may be bonded to each other, to form a saturated orunsaturated ring.

Specific examples of the alkyl group include a methyl group, an ethylgroup, a propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, ann-hexyl group, an n-heptyl group, an n-octyl group, a hydroxymethylgroup, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, and a1,2,3-trihydroxypropyl group. Preferred are a methyl group, an ethylgroup, a propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, and a tert-butyl group.

Specific examples of the cycloalkyl group include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, acyclopentylmethyl group, a cyclohexylmethyl group, a cyclohexylethylgroup, a 4-fluorocyclohexyl group, a 1-adamantyl group, a 2-adamantylgroup, a 1-norbornyl group, and a 2-norbornyl group. Preferred are acyclopentyl group and a cyclohexyl group.

Specific examples of the trialkylsilyl group include a trimethylsilylgroup, a vinyldimethylsilyl group, a triethylsilyl group, atripropylsilyl group, a propyldimethylsilyl group, a tributylsilylgroup, a t-butyldimethylsilyl group, a tripentylsilyl group, atriheptylsilyl group, and a trihexylsilyl group. Preferred are atrimethylsilyl group and a triethylsilyl group. A silyl group may besubstituted with alkyl groups identical to or different from each other.

Specific examples of the triarylsilyl group include a triphenylsilylgroup, a trinaphthylsilyl group, and a trianthrylsilyl group. Preferredis a triphenylsilyl group. A silyl group may be substituted with arylgroups identical to or different from each other.

Specific examples of the alkylarylsilyl group include adimethylphenylsilyl group, a diethylphenylsilyl group, adipropylphenylsilyl group, a dibutylphenylsilyl group, adipentylphenylsilyl group, a diheptylphenylsilyl group, adihexylphenylsilyl group, a dimethylnaphthylsilyl group, adipropylnaphthylsilyl group, a dibutylnaphthylsilyl group, adipentylnaphthylsilyl group, a diheptylnaphthylsilyl group, adihexylnaphthylsilyl group, a dimethylanthrylsilyl group, adiethylanthrylsilyl group, a dipropylanthrylsilyl group, adibutylanthrylsilyl group, a dipentylanthrylsilyl group, adiheptylanthrylsilyl group, a dihexylanthrylsilyl group, and adiphenylmethyl group. Preferred are a dimethylphenylsilyl group, adiethylphenylsilyl group, and a diphenylmethyl group.

Specific examples of the aryl group include a phenyl group, a2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a4-ethylphenyl group, a biphenylyl group, a 4-methylbiphenylyl group, a4-ethylbiphenylyl group, a 4-cyclohexylbiphenylyl group, an anthracenylgroup, a naphthacenyl group, a terphenyl group, a triphenylyl group, a3,5-dichlorophenylyl group, a naphthyl group, a 5-methylnaphthyl group,a phenanthryl group, a chrysenyl group, a benzophenanthryl group, aterphenyl group, a benzanthranyl group, a benzochrysenyl group, apentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group,a chrysenyl group, a fluorenyl group, an indenyl group, anacenaphthylenyl group, a fluoranthenyl group, and a perylenyl group.Preferred are a phenyl group, a biphenylyl group, and a naphthyl group.Specific examples of the halogen atom include fluorine, chlorine, andbromine.

Specific examples of the saturated or unsaturated ring which theplurality of R¹'s to R⁶'s are bonded to themselves, or R¹ and R², R³ andR⁴, or R⁵ and R⁶ are bonded to each other, to form include the arylgroups and cycloalkyl groups, and heteroaryl groups to be describedlater.

The skeletal structure of the substituent A represented by the generalformula (1) from which L¹, R¹, and R² are removed, and the skeletalstructure of the substituent B represented by the general formula (2)from which L², R³, and R⁴ are removed and in which X represents anoxygen atom are specifically, for example, the following skeletalstructures.

In the general formulae (1) to (3), (1-1) to (1-3), and (2-1):

a, c, e, and f each independently represent an integer of 0 to 3, and band d each independently represent an integer of 0 to 4; and

L¹ and L² each independently represent a single bond, or a substitutedor unsubstituted arylene group having 6 to 50, preferably 6 to 21, morepreferably 6 to 15, ring carbon atoms, and L³ represents a substitutedor unsubstituted arylene group having 6 to 50, preferably 6 to 21, morepreferably 6 to 15, ring carbon atoms, provided that a substituent whichany one of L¹ to L³ may have is a linear or branched alkyl group having1 to 10, preferably 1 to 6, carbon atoms, a cycloalkyl group having 3 to10, preferably 5 to 7, ring carbon atoms, a trialkylsilyl group having 3to 10, preferably 3 to 6, carbon atoms, a triarylsilyl group having 18to 30, preferably 18 to 24, ring carbon atoms, an alkylarylsilyl grouphaving 8 to 15, preferably 8 to 12, carbon atoms (its aryl portion has 6to 14, preferably 6 to 12, ring carbon atoms), an aryl group having 6 to16, preferably 6 to 10, ring carbon atoms, a halogen atom (a fluorineatom is preferred), or a cyano group.

When the linking groups L¹ and L² are single bonds, and a dibenzofuranstructure or a carbazole structure is directly bonded to a nitrogenatom, the electron density of the amine compound increases and the IP ofthe compound can be reduced. On the other hand, when any such structureis bonded to a nitrogen atom through the linking group L¹ or L² servingas a substituted or unsubstituted arylene group, an increase in theelectron density of the amine compound is suppressed and the IP can beincreased.

When the aromatic amine derivative is represented by the general formula(5) to be described later, L¹ and L² each preferably represent asubstituted or unsubstituted arylene group.

That is, the IP of the amine compound can be adjusted by selecting thelinking groups L¹ and L². When the IP is set to a value suitable as ahole injecting material or hole transporting material, the property bywhich holes are injected into the light emitting layer is improved, andhence a reduction in the voltage at which the device is driven can beexpected.

Specific examples of the arylene group represented by any one of L¹ toL³ include arylene groups such as a phenylene group, a biphenylenegroup, a terphenylene group, a tetrafluorophenylene group, adimethylphenylene group, a naphthylene group, an anthranylene group, aphenanthrylene group, a pyrenylene group, a naphthacenylene group, aquarterphenylene group, a pentacenylene group, a perylenylene group, apyrenylene group, a coronylene group, a fluorenylene group, anacenaphthofluorenylene group, and a 9,9-dimethylfluorenylene group.

In the general formulae (1) to (3), (1-1) to (1-3), and (2-1), anarylene group represented by any one of L¹ to L³ is preferablyrepresented by any one of the following general formulae (4), (10), and(11).

In each of the general formulae (2) and (2-1) in the case where Xrepresents a —N(Ar¹)— group, when an arylene group represented by L² isrepresented by the general formula (4), an increase in the electrondensity of the amine compound is suppressed, and as a result, the IPincreases. When the compound is used as a hole transporting material,the property by which holes are injected into the light emitting layeris improved, and hence a reduction in the voltage at which the device isdriven can be expected. In particular, when the aromatic aminederivative of the present invention has a dibenzofuranstructure-containing group and a carbazole structure-containing group,specifically, when the derivative has the substituent A represented bythe general formula (1) and the substituent B represented by the generalformula (2-1) or (3), an arylene group represented by L₂ or L₃ in thesubstituent B is preferably represented by the general formula (4).

When the substituent B is represented by the general formula (3), animprovement in the luminous efficiency, and the lengthening of thelifetime, of the device can be expected because the aromatic aminederivative has so large an energy gap as to be capable of suppressingthe injection of electrons into a hole transporting layer. Inparticular, when the aromatic amine derivative is an amine having thesubstituent A having a dibenzofuran structure and the substituent Bhaving a carbazole structure, the substituent B is preferablyrepresented by the general formula (3).

When the aromatic amine derivative of the present invention has theplurality of substituents A, the plurality of substituents A arepreferably groups different from each other. In addition, when thearomatic amine derivative of the present invention has the plurality ofsubstituents B, the plurality of substituents B are preferably groupsdifferent from each other. When the substituents A and/or thesubstituents B are groups different from each other, the molecularsymmetry can be further reduced, and hence additional suppression of thecrystallization can be expected.

In addition, the substituent having a dibenzofuran structure ispreferably represented by the formula (1-1) or (1-2) out of the formulae(1-1), (1-2), and (1-3) from the viewpoints of the ease of synthesis andthe ease of purification.

In the general formulae (4), (10), and (11), R⁷ to R¹¹ eachindependently represent a linear or branched alkyl group having 1 to 10,preferably 1 to 6, carbon atoms, a cycloalkyl group having 3 to 10,preferably 5 to 7, ring carbon atoms, a trialkylsilyl group having 3 to10, preferably 3 to 6, carbon atoms, a triarylsilyl group having 18 to30, preferably 18 to 24, ring carbon atoms, an alkylarylsilyl grouphaving 8 to 15, preferably 8 to 12, carbon atoms (its aryl portion has 6to 14, preferably 6 to 10, ring carbon atoms), an aryl group having 6 to14, preferably 6 to 10, ring carbon atoms, a halogen atom (a fluorineatom is preferred), or a cyano group, and a plurality of R⁷'s to R¹¹'sadjacent to each other may be bonded to each other to form a saturatedor unsaturated ring.

Specific examples and preferred examples of the alkyl group, cycloalkylgroup, trialkylsilyl group, triarylsilyl group, alkylarylsilyl group,aryl group, and halogen atom each represented by any one of R⁷ to R¹¹ inthe general formulae (4), (10), and (11) are the same as those listed inthe description of the R¹ to R¹⁶. R⁷ To R¹¹ each preferably represent amethyl group, an ethyl group, a propyl group, an isopropyl group, ann-butyl group, an isobutyl group, an sec-butyl group, or a tert-butylgroup.

In the general formula (11), R¹² and R¹³ each independently represent alinear or branched alkyl group having 1 to 10, preferably 1 to 6, carbonatoms, or a cycloalkyl group having 3 to 10, preferably 5 to 7, ringcarbon atoms. Specific examples and preferred examples of the alkylgroup and cycloalkyl group are the same as those listed in thedescription of the R¹ to R⁶.

In the general formulae (4), (10), and (11), g, h, and i eachindependently represent an integer of 0 to 4, preferably an integer of 0or 1, and j and k each independently represent an integer of 0 to 3,preferably an integer of 0 or 1.

The substituents of L¹ to L⁶ in the general formulae (1) to (3), (1-1)to (1-3), and (2-1) are each a linear or branched alkyl group having 1to 10, preferably 1 to 6, carbon atoms, a cycloalkyl group having 3 to10, preferably 5 to 7, ring carbon atoms, a trialkylsilyl group having 3to 10, preferably 3 to 6, ring carbon atoms, a triarylsilyl group having18 to 30, preferably 18 to 24, ring carbon atoms, an alkylarylsilylgroup having 8 to 15, preferably 8 to 12, carbon atoms (its aryl portionhas 6 to 14, preferably 6 to 10, ring carbon atoms), an aryl grouphaving 6 to 14, preferably 6 to 10, ring carbon atoms, a halogen atom,or a cyano group.

Specific examples and preferred examples of the alkyl group, cycloalkylgroup, trialkylsilyl group, triarylsilyl group, alkylarylsilyl group,aryl group, and halogen atom are the same as those listed in thedescription of the R¹ to R⁶.

Preferred specific examples of the general formulae (8) to (10) includea substituted or unsubstituted phenylene group, a substituted orunsubstituted biphenylene group, and a substituted or unsubstituted9,9-dimethylfluorenylene group.

In the general formula (2), Ar¹ represents a substituted orunsubstituted aryl group having 6 to 14, preferably 6 to 10, ring carbonatoms. Specific examples and preferred examples of the aryl group arethe same as those listed in the description of the R¹ to R⁶.

The substituents of the aryl group are each independently a linear orbranched alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, acycloalkyl group having 3 to 10, preferably 5 to 7, ring carbon atoms, atrialkylsilyl group having 3 to 10, preferably 3 to 6, carbon atoms, atriarylsilyl group having 18 to 30, preferably 18 to 24, ring carbonatoms, an alkylarylsilyl group having 8 to 15, preferably 8 to 12,carbon atoms (its aryl portion has 6 to 14 ring carbon atoms), an arylgroup having 6 to 16, preferably 6 to 10, ring carbon atoms, a halogenatom (a fluorine atom is preferred), or a cyano group.

Specific examples and preferred examples of the alkyl group, cycloalkylgroup, trialkylsilyl group, triarylsilyl group, alkylarylsilyl group,and aryl group are the same as those listed in the description of the R¹to R⁶.

Next, the compounds represented by the general formulae (5) to (9) aredescribed.

In the general formula (5), at least one of Ar² to Ar⁴ represents thesubstituent A represented by the general formula (1), at least one ofAr² to Ar⁴ represents the substituent B represented by the generalformula (2) or (3), and the substituent A and the substituent B aregroups different from each other.

In the general formula (6), at least one of Ar⁵ to Ar⁸ represents thesubstituent A represented by the general formula (1), at least one ofAr⁵ to Ar⁸ represents the substituent B represented by the generalformula (2) or (3), and the substituent A and the substituent B aregroups different from each other.

In the general formula (7), at least one of Ar⁹ to Ar¹³ represents thesubstituent A represented by the general formula (1), at least one ofAr⁹ to Ar¹³ represents the substituent B represented by the generalformula (2) or (3), and the substituent A and the substituent B aregroups different from each other.

In the general formula (8), at least one of Ar¹⁴ to Ar¹⁹ represents thesubstituent A represented by the general formula (1), at least one ofAr¹⁴ to Ar¹⁹ represents the substituent B represented by the generalformula (2) or (3), and the substituent A and the substituent B aregroups different from each other.

In the general formula (9), at least one of Ar²⁰ to Ar²⁵ represents thesubstituent A represented by the general formula (1), at least one ofAr²⁰ to Ar²⁵ represents the substituent B represented by the generalformula (2) or (3), and the substituent A and the substituent B aregroups different from each other.

In the general formulae (3) to (7), groups out of Ar² to Ar²⁵ except thesubstituent A and the substituent B are each independently a substitutedor unsubstituted aryl group having 6 to 50, preferably 6 to 21, morepreferably 6 to 14, ring carbon atoms, and specific examples andpreferred examples of the aryl group are the same as those listed in thedescription of the R¹ to R⁶. The aryl group is particularly preferably aterphenyl group. When the aromatic amine derivative has a terphenylgroup excellent in reduction stability, the reduction stability of anyone of its molecules is improved, and a lengthening effect on thelifetime of an organic EL device to be obtained is exerted. Inparticular, a combination of the derivative and a blue light emittingdevice exerts a significant lifetime-lengthening effect.

Specific examples and preferred examples of the substituents of Ar² toAr²⁵ are the same as those listed in the description of the R¹ to R⁶.

In the general formulae (5) to (9), L⁴ to L¹² each independentlyrepresent a substituted or unsubstituted arylene group having 6 to 50,preferably 6 to 21, more preferably 6 to 15, ring carbon atoms. Specificexamples and preferred examples of the arylene group represented by anyone of L⁴ to L¹² are the same as those listed in L¹ to L³ described forthe general formulae (1) to (3), (1-1) to (1-3), and (2-1).

When Ar² to Ar²⁵ in the general formulae (5) to (9) are each thesubstituent A or the substituent B, R¹ to R⁶, L¹ to L³, and a to f inthe general formulae (1) to (3), (1-1) to (1-3), and (2-1) are asdescribed for the aromatic amine derivative represented by the generalformula (1).

The aromatic amine derivative represented by any one of the generalformulae (5) to (9) is preferably a compound having any such combinationas described below.

(I) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² is represented by the generalformula (1), and the Ar³ and the Ar⁴ are each independently representedby the general formula (3) or (2-1).

(II) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² and the Ar³ are each represented bythe general formula (1), and the Ar⁴ is represented by the generalformula (3) or (2-1).

(III) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² is represented by the generalformula (1), the Ar³ is represented by the general formula (3) or (2-1),and the Ar⁴ represents a substituted or unsubstituted aryl group having6 to 50 ring carbon atoms, provided that substituents of the Ar⁴ eachindependently include any one of an aryl group having 6 to 50 ringcarbon atoms, a branched or linear alkyl group having 1 to 50 carbonatoms, a halogen atom, and a cyano group.

(IV) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (6) in which the Ar⁵ and the Ar⁶ are each represented bythe general formula (1), and the Ar⁷ and the Ar⁸ are each independentlyrepresented by the general formula (3) or (2-1).

(V) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (6) in which the Ar⁵ and the Ar⁷ are each represented bythe general formula (1), and the Ar⁶ and the Ar⁸ are each independentlyrepresented by the general formula (3) or (2-1).

(VI) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (7) in which the Ar⁹ is represented by the generalformula (1), and the Ar¹¹ and the Ar¹² are each independentlyrepresented by the general formula (3) or (2-1).

(VII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (7) in which the Ar¹¹ and the Ar¹² are each representedby the general formula (1), and the Ar⁹ is represented by the generalformula (3) or (2-1).

(VIII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (8) in which the Ar¹⁴ and the Ar¹⁹ are each representedby the general formula (1), and the Ar¹⁶ and the Ar¹⁷ are eachindependently represented by the general formula (3) or (1).

(IX) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (8) in which the Ar¹⁶ and the Ar¹⁷ are each representedby the general formula (1-1), and the Ar¹⁴ and the Ar¹⁹ are eachindependently represented by the general formula (3) or (2-1).

(X) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (9) in which the Ar²⁰, the Ar²², and the Ar²⁴ are eachrepresented by the general formula (1), and the Ar²¹, the Ar²³, and theAr²⁵ are each independently represented by the general formula (3) or(2-1).

(XI) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² to Ar⁴ are each represented by thegeneral formula (1-3).

(XII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² to Ar⁴ are each represented by thegeneral formula (1-1).

(XIII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which two of the Ar² to Ar⁴ are each representedby the general formula (1-3), and one of the Ar² to Ar⁴ represents asubstituted or unsubstituted aryl group having 6 to 16 ring carbonatoms.

(XIV) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which two of the Ar² to Ar⁴ are each representedby the general formula (1-1), and one of the Ar² to Ar⁴ represents asubstituted or unsubstituted aryl group having 6 to 16 ring carbonatoms.

(XV) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which at least one of the Ar² to Ar⁴ isrepresented by the general formula (1-3), and at least one of the Ar² toAr⁴ is represented by the general formula (1-1).

(XVI) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² is represented by the generalformula (1-3), and the Ar³ and the Ar⁴ are each independentlyrepresented by the general formula (1-1).

(XVII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar² and the Ar³ are each represented bythe general formula (1-3), and the Ar⁴ is represented by the generalformula (1-1).

(XVIII) The aromatic amine derivative, in which at least two of the Ar⁵to Ar⁸ are each, at least two of the Ar⁹ to Ar¹³ are each, at least oneof the Ar¹⁴ to Ar¹⁹ is, or at least one of the Ar²⁰ to Ar²⁵ isrepresented by the general formula (1-3) or the general formula (1-1).

(XIX) The aromatic amine derivative, in which the aromatic aminederivative includes any one of an aromatic amine derivative representedby the general formula (6) in which at least one of the Ar⁵ to Ar⁸ isrepresented by the general formula (1-3) and at least one of the Ar⁵ toAr⁸ except the at least one represented by the general formula (1-3) isrepresented by the general formula (1-1), an aromatic amine derivativerepresented by the general formula (7) in which at least one of the Ar⁹to Ar¹³ is represented by the general formula (1-3) and at least one ofthe Ar⁹ to Ar¹³ except the at least one represented by the generalformula (1-3) is represented by the general formula (1-1), an aromaticamine derivative represented by the general formula (8) in which atleast one of the Ar¹⁴ to Ar¹⁹ is represented by the general formula(1-3) and at least one of the Ar¹⁴ to Ar¹⁹ except the at least onerepresented by the general formula (1-3) is represented by the generalformula (1-1), and an aromatic amine derivative represented by thegeneral formula (9) in which at least one of the Ar²⁰ to Ar²⁵ isrepresented by the following general formula (1-3) and at least one ofthe Ar²⁰ to Ar²⁵ except the at least one represented by the generalformula (1-3) is represented by the following general formula (1-1).

(XX) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar⁵ is represented by the generalformula (1-3) and the Ar⁶ is represented by the general formula (1-1).

(XXI) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (5) in which the Ar⁵ and the Ar⁷ are each represented bythe general formula (1-3) and the Ar⁶ and the Ar⁸ are each representedby the general formula (1-1).

(XXII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (6) in which the Ar⁹ is represented by the generalformula (1-3) and the Ar¹¹ and the Ar¹² are each represented by thegeneral formula (1-1).

(XXIII) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (6) in which the Ar¹⁰ and the Ar¹³ are each representedby the general formula (1-3) and the Ar¹¹ and the Ar¹² are eachrepresented by the general formula (1-1).

(XXIV) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (8) in which the Ar¹⁴ and the Ar¹⁹ are each representedby the general formula (1-3) and the Ar¹⁶ and the Ar¹⁷ are eachrepresented by the general formula (1-1).

(XXV) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (8) in which the Ar¹⁵ and the Ar¹⁸ are each representedby the general formula (1-3) and the Ar¹⁶ and the Ar¹⁷ are eachrepresented by the general formula (1-1).

(XXVI) The aromatic amine derivative, in which the aromatic aminederivative includes an aromatic amine derivative represented by thegeneral formula (9) in which the Ar²⁰, the Ar²², and the Ar²⁴ are eachrepresented by the general formula (1-3) and the Ar²¹, the Ar²³, and theAr²⁵ are each represented by the general formula (1-1).

(XXVII) The aromatic amine derivative, in which groups out of the Ar² toAr²⁵ except the substituent A and the substituent B each independentlyrepresent a phenyl group, a naphthyl group, a biphenyl group, aterphenyl group, or a fluorenyl group.

Specific examples of the aromatic amine derivative represented by anyone of the general formulae (5) to (9) include the following compounds.

The aromatic amine derivative of the present invention hardlycrystallizes, and is preferably used as a light emitting material for anorganic EL device, in particular, as a hole transporting material for anorganic EL device. An organic EL device using the aromatic aminederivative of the present invention not only provides high efficiencyeven at high temperatures but also has a long lifetime.

Next, a method of producing the aromatic amine derivative of the presentinvention is described.

The method of producing the aromatic amine derivative of the presentinvention is not particularly limited, and is, for example, as describedbelow.

(Production Method 1)

The aromatic amine derivative of the present invention represented bythe general formula (5) can be synthesized by, for example, any suchreaction as described below.

(a) Synthesis of an Aromatic Amine Derivative in which all of Ar² to Ar⁴Each Represent the Substituent A or the Substituent B

First, compounds that produce a structure represented by the generalformula (1) [such as dibenzofuran-4-boronic acid and 4-iodobromobenzene]are caused to react with each other in the presence of a catalyst [suchas tetrakis(triphenylphosphine)palladium(0)] in a solvent [such astoluene] and an aqueous solution of an alkaline compound [such as sodiumcarbonate] at 50 to 150° C. Thus, a halide is obtained. Further, theabove-mentioned halide and a compound that produces an amino group [suchas acetamide] are caused to react with each other in the presence ofcatalysts [a metal halide such as copper iodide and an amine such asN,N′-dimethylethylenediamine] and an alkaline substance [such aspotassium carbonate] in a solvent [such as xylene] at 50 to 250° C.After that, the resultant is subjected to a reaction in the presence ofan alkaline substance [such as potassium carbonate] and water in asolvent [such as xylene] at 50 to 250° C. Thus, an intermediate X issynthesized. The reactions are preferably performed under an atmosphereof an inert gas such as argon.

Separately, halides that produce a structure represented by the generalformula (3) [such as carbazole and 4-iodobromobenzene] are caused toreact with each other in the presence of catalysts [such as copperiodide (CuI) and an amine such as trans-1,2-cyclohexanediamine] in asolvent [such as 1,4-dioxane] and an alkaline compound [such astripotassium phosphate] at 50 to 150° C. Thus, an intermediate Y issynthesized. The reaction is preferably performed under an atmosphere ofan inert gas such as argon.

Next, the intermediate X and the intermediate Y are caused to react witheach other in the presence of catalysts [such as t-butoxy sodium andtris(dibenzylideneacetone)dipalladium(0)] in a solvent [such as drytoluene] at 0 to 150° C. Thus, the aromatic amine derivative of thepresent invention can be synthesized. The reaction is preferablyperformed under an atmosphere of an inert gas such as argon.

After the completion of the reaction, the reaction product is cooled toroom temperature, and then water is added to filtrate the product. Thefiltrate is extracted with a solvent such as toluene, and is then driedwith a drying agent such as anhydrous magnesium sulfate. The driedproduct is desolvated under reduced pressure so as to be concentrated.The resultant coarse product is subjected to column purification, and isthen recrystallized with a solvent such as toluene. The crystal isseparated by filtration, and is then dried. Thus, the aromatic aminederivative of the present invention that has been purified is obtained.

In order that the general formula (1) and the general formula (2-1) maybe introduced into the aromatic amine derivative represented by thegeneral formula (5), upon synthesis of the above-mentioned intermediateY, halides that produce a structure represented by the general formula(2-1) [such as 9-phenylcarbazole and iodine] are caused to react witheach other in the presence of catalysts [such as periodic aciddihydrate, acetic acid, and sulfuric acid] in a solvent [such as water]at 50 to 100° C. so that the intermediate Y capable of introducing thegeneral formula (2-1) may be synthesized. Next, the intermediate X andthe intermediate Y are caused to reach with each other in the samemanner as in the foregoing. Thus, the aromatic amine derivative of thepresent invention into which the general formula (1) and the generalformula (2-1) have been introduced can be synthesized. The reactions arepreferably performed under an atmosphere of an inert gas such as argon.

(b) Synthesis of an Aromatic Amine Derivative in which One of Ar² to Ar⁴has a Group Except the General Formula (1), (2-1), or (3)

In order that a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms except the general formula (1), (2-1), or (3) may beintroduced into the aromatic amine derivative represented by the generalformula (5), the introduction has only to be performed as describedbelow. Upon synthesis of the intermediate X or at the time of thereaction between the intermediate X and the intermediate Y, a reactingweight ratio is controlled, and halides of substituted or unsubstitutedaryl groups each having 6 to 50 ring carbon atoms except the generalformula (1) and the general formula (3) [such as 4-bromo-p-terphenyl]are similarly subjected to reactions in sequence [for example, afteracetamide and 4-(4-iodophenyl)-dibenzofuran have been caused to reactwith each other at 1:1, 1 equivalent of 4-bromo-p-terphenyl is loadedand caused to react with the reaction product, followed by thehydrolysis of the resultant, and as a result, the intermediate X intowhich the general formula (1-1) and the “aryl group except the generalformulae (1-1), (1-2), and (2)” have been introduced is obtained].

A halide represented by the general formula (1), a halide represented bythe general formula (3), and a halide of a substituted or unsubstitutedaryl group having 6 to 50 ring carbon atoms except the general formula(1) and the general formula (3) can be arbitrarily introduced into theintermediate X. In addition, one or two aryl groups can be introduced,and further, an arbitrary combination of aryl groups can be introduced.A target product can be obtained by causing the amine compound(intermediate X) obtained as a result of the introduction and anarbitrary halide (intermediate Y) to react with each other. The order inwhich those halides are subjected to reactions and the manner in whichthe halides are combined can be determined in consideration of, forexample, reactivity and the ease of purification.

Next, a method of producing the aromatic amine derivative represented bythe general formula (6) is described.

(a) Synthesis of an Aromatic Amine Derivative in which all of Ar⁵ to Ar⁸Each Have a Group Represented by the General Formula (1), (2-1), or (3)

An amine compound including the general formula (1) and the generalformula (3) is synthesized as the intermediate X in the same manner asin the foregoing [for example, after acetamide and4-(4-iodophenyl)-dibenzofuran have been caused to react with each otherat 1:1, 1 equivalent of 9-(4-bromo-phenyl)carbazole is loaded and causedto react with the reaction product, followed by the hydrolysis of theresultant, and as a result, the intermediate X into which the generalformula (1) and the general formula (3) have been introduced isobtained].

A dihalide [such as 4,4′-dibromobiphenyl] serving as a halide is used asthe intermediate Y. The intermediate X and the intermediate Y are causedto react with each other at 0 to 150° C. in the same manner as in theforegoing. Thus, the aromatic amine derivative in which all of Ar⁵ toAr⁸ in the general formula (6) are each represented by the generalformula (1), (2-1), or (3) can be synthesized.

(b) Synthesis of an Aromatic Amine Derivative in which at Least One ofAr⁵ to Ar⁸ has a Group Except the General Formula (1), (2-1), or (3)

An amine compound including the general formula (1) and the generalformula (3) is synthesized as the intermediate X in the same manner asin the foregoing [for example, after acetamide and4-(4-iodophenyl)-dibenzofuran have been caused to react with each otherat 1:1, 1 equivalent of 9-(4-bromo-phenyl)carbazole is loaded and causedto react with the reaction product, followed by the hydrolysis of theresultant, and as a result, the intermediate X into which the generalformula (1) and the general formula (3) have been introduced isobtained].

An amino group-containing compound [such as 4-bromophenyl-diphenylamine]serving as a halide is used as the intermediate Y. The intermediate Xand the intermediate Y are caused to react with each other at 0 to 150°C. in the same manner as in the foregoing. Thus, the aromatic aminederivative in which at least one of Ar⁵ to Ar⁸ in the general formula(6) is represented by a group except the general formula (1), (2-1), or(3) can be synthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (7) is described.

An amine compound including the general formula (1) is synthesized asthe intermediate X in the same manner as in the foregoing [for example,after acetamide and 4-(4-iodophenyl)-dibenzofuran have been caused toreact with each other at 1:1, the reaction product is hydrolyzed, and asa result, the intermediate X into which the general formula (1) has beenintroduced is obtained]. An amino group-containing compound serving as ahalide is synthesized as the intermediate Y [for example, after anilineand carbazole have been caused to react with each other at 1:1, thereaction product and 4′-iodobromobiphenyl are further caused to reactwith each other at 1:1, and as a result, the intermediate Y into whichthe general formula (3) has been introduced is obtained]. Theintermediate X and the intermediate Y are caused to react with eachother at 0 to 150° C. in the same manner as in the foregoing. Thus, thearomatic amine derivative represented by the general formula (7) can besynthesized. The number and kinds of substituents of Ar¹¹ to Ar¹⁵ can bechanged by changing a starting material and a reaction intermediate. Inaddition, an aromatic amine derivative in which all of Ar¹¹ to Ar¹⁵ eachhave a group represented by the general formula (1), (2-1), or (3) canbe synthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (8) is described.

An amine compound including the general formula (1) is synthesized asthe intermediate X in the same manner as in the foregoing [for example,after acetamide and 4-(4-iodophenyl)-dibenzofuran have been caused toreact with each other at 1:1, the reaction product and4,4′-diiodobiphenyl are caused to react with each other at 2:1, followedby the hydrolysis of the resultant, and as a result, the intermediate Xas a diamine compound into which the general formula (1) has beenintroduced is obtained].

An amino group-containing compound serving as a halide is synthesized asthe intermediate Y [for example, after aniline and carbazole have beencaused to react with each other at 1:1, the reaction product and4′-iodobromobenzene are further caused to react with each other at 1:1,and as a result, the intermediate Y into which the general formula (3)has been introduced is obtained]. The intermediate X and theintermediate Y are caused to react with each other at 0 to 150° C. inthe same manner as in the foregoing. Thus, the aromatic amine derivativerepresented by the general formula (8) can be synthesized. The numberand kinds of substituents of Ar¹⁴ to Ar¹⁹ can be changed by changing astarting material and a reaction intermediate. In addition, an aromaticamine derivative in which all of Ar¹⁴ to Ar¹⁹ each have a grouprepresented by the general formula (1), (2-1), or (3) can besynthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (9) is described.

An amine compound including the general formula (1) is synthesized asthe intermediate X in the same manner as in the foregoing [for example,after acetamide and 4-(4-iodophenyl)-dibenzofuran have been caused toreact with each other at 1:1, 1 equivalent of9-(4-bromo-phenyl)carbazole is loaded and caused to react with thereaction product, followed by the hydrolysis of the resultant, and as aresult, the intermediate X into which the general formula (1) and thegeneral formula (3) have been introduced is obtained].

An amino group-containing compound serving as a halide is used as theintermediate Y [such as commercially availabletris(4-bromophenyl)amine]. The intermediate X and the intermediate Y arecaused to react with each other at 0 to 150° C. in the same manner as inthe foregoing. Thus, the aromatic amine derivative represented by thegeneral formula (9) can be synthesized. The number and kinds ofsubstituents of Ar²² to Ar²⁷ can be changed by changing a startingmaterial and a reaction intermediate. In addition, an aromatic aminederivative in which all of Ar²² to Ar²⁷ each have a group represented bythe general formula (1), (2-1), or (3) can be synthesized.

In addition, individual, similar synthesis methods described in knowntechnologies (JP 2003-171366 A, WO 2006/114921 A1, WO 2006/073054 A1, WO2007/125714 A1, and WO 2008/062636 A1) may each be employed for any suchsynthesis as described above.

(Production Method 2)

The aromatic amine derivative of the present invention represented bythe general formula (5) can be synthesized by, for example, any suchreaction as described below.

First, compounds that produce a structure represented by the generalformula (1-2) [such as dibenzofuran-4-boronic acid and4-iodobromobenzene] are caused to react with each other in the presenceof a catalyst [such as tetrakis(triphenylphosphine)palladium(0)] in asolvent [such as toluene] and an aqueous solution of an alkalinecompound [such as sodium carbonate] at 50 to 150° C. Thus, a halide isobtained. Further, the above-mentioned halide and a compound thatproduces an amino group [such as acetamide] are caused to react witheach other in the presence of catalysts [a metal halide such as copperiodide and an amine such as N,N′-dimethylethylenediamine] and analkaline substance [such as potassium carbonate] in a solvent [such asxylene] at 50 to 250° C. After that, the resultant is subjected to areaction in the presence of an alkaline substance [such as potassiumhydroxide] and water in a solvent [such as xylene] at 50 to 250° C.Thus, an intermediate X is synthesized. The reactions are preferablyperformed under an atmosphere of an inert gas such as argon.

Separately, halides that produce a structure represented by the generalformula (1-1) [such as dibenzofuran-2-boronic acid and4-iodobromobenzene] are caused to react with each other in the presenceof a catalyst [such as tetrakis(triphenylphosphine)palladium(0)] in asolvent [such as toluene] and an aqueous solution of an alkalinecompound [such as sodium carbonate] at 50 to 150° C. Thus, anintermediate Y is synthesized. The reaction is preferably performedunder an atmosphere of an inert gas such as argon.

Next, the intermediate X and the intermediate Y are caused to react witheach other in the presence of catalysts [such as t-butoxy sodium andtris(dibenzylideneacetone)dipalladium(0)] in a solvent [such as drytoluene] at 0 to 150° C. Thus, the aromatic amine derivative of thepresent invention can be synthesized. The reaction is preferablyperformed under an atmosphere of an inert gas such as argon.

After the completion of the reaction, the reaction product is cooled toroom temperature, and then water is added to filtrate the product. Thefiltrate is extracted with a solvent such as toluene, and is then driedwith a drying agent such as anhydrous magnesium sulfate. The driedproduct is desolvated under reduced pressure so as to be concentrated.The resultant coarse product is subjected to column purification, and isthen recrystallized with a solvent such as toluene. The crystal isseparated by filtration, and is then dried. Thus, the aromatic aminederivative of the present invention that has been purified is obtained.

Described above is a method of producing the aromatic amine derivativein which Ar² and Ar³ are each represented by the general formula (1-2),and Ar⁴ is represented by the general formula (1-1). It should be notedthat an aromatic amine derivative in which Ar² is represented by thegeneral formula (1-2), and Ar³ and Ar⁴ are each represented by thegeneral formula (1-1) can be produced by a similar method. In this case,the derivative can be produced by synthesizing the intermediate X withthe general formula (1-2), synthesizing the intermediate Y with thegeneral formula (1-1), and causing the intermediate X and theintermediate Y to react with each other in the above-mentionedproduction.

In addition, similar synthesis can be performed even in the case whereall of Ar² to Ar⁴ represented by the general formula (1-2) and/or thegeneral formula (1-1) are different from one another. In order that Ar²to Ar⁴ that are different from one another may be introduced, theintroduction has only to be performed as described below. Upon synthesisof the intermediate X or at the time of the reaction between theintermediate X and the intermediate Y, a reacting weight ratio iscontrolled, and a halide are similarly subjected to reactions insequence [for example, after acetamide and4-(4-bromophenyl)-dibenzofuran have been caused to react with each otherat 1:1, 1 equivalent of 2-(4-bromophenyl)-dibenzofuran is loaded andcaused to react with the reaction product, followed by the hydrolysis ofthe resultant, and as a result, the intermediate X into which thegeneral formula (1-2) and the general formula (1-1) have been introducedis obtained]. After that, the intermediate X and the intermediate Y as ahalide different from the substituents that have already been introduced[such as 4-(4-bromobiphenyl)-dibenzofuran] are caused to react with eachother. Thus, the synthesis can be achieved.

A halide represented by the general formula (1-2) and a haliderepresented by the general formula (1-1) can be arbitrarily introducedinto the intermediate X. A target product can be obtained by causing theamine compound (intermediate X) obtained as a result of the introductionand an arbitrary halide (intermediate Y) to react with each other. Theorder in which those halides are subjected to reactions and the mannerin which the halides are combined can be determined in consideration of,for example, reactivity and the ease of purification.

Next, a method of producing the aromatic amine derivative represented bythe general formula (6) is described.

An amine compound including the general formula (1-2) and the generalformula (1-1) is synthesized as the intermediate X in the same manner asin the foregoing [for example, after acetamide and4-(4-bromophenyl)-dibenzofuran have been caused to react with each otherat 1:1, 1 equivalent of 2-(4-bromophenyl)-dibenzofuran is loaded andcaused to react with the reaction product, followed by the hydrolysis ofthe resultant, and as a result, the intermediate X into which thegeneral formula (1-2) and the general formula (1-1) have been introducedis obtained].

A dihalide [such as 4,4′-dibromobiphenyl] serving as a halide is used asthe intermediate Y. The intermediate X and the intermediate Y are causedto react with each other at 0 to 150° C. in the same manner as in theforegoing. Thus, the aromatic amine derivative in which all of Ar⁷ toAr¹⁰ in the general formula (6) are each represented by the generalformula (1-2) or (1-1) can be synthesized.

Alternatively, an amino group-containing compound [such as4-bromophenyl-diphenylamine] serving as a halide is used as theintermediate Y, and the intermediate X and the intermediate Y are causedto react with each other at 0 to 150° C. in the same manner as in theforegoing. Thus, the aromatic amine derivative in which at least one ofAr⁷ to Ar¹⁰ in the general formula (6) is represented by a group exceptthe general formula (1-2) or (1-1) can be synthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (7) is described.

An amine compound (such as commercially available aniline) is used asthe intermediate X.

In addition, a halogen compound containing an amine compound includingthe general formula (1-2) and the general formula (1-1) is synthesizedas the intermediate Y in the same manner as in the foregoing [forexample, after acetamide and 4-(4-bromophenyl)-dibenzofuran have beencaused to react with each other at 1:1, 1 equivalent of2-(4-bromophenyl)-dibenzofuran is loaded and caused to react with thereaction product, followed by the hydrolysis of the resultant, and as aresult, the amine compound into which the general formula (1-2) and thegeneral formula (1-1) have been introduced is obtained. Further, theamine compound and 4′-iodobromobiphenyl are caused to react with eachother at 1:1, and as a result, the intermediate Y into which the generalformula (1-2) and the general formula (1-1) have been introduced isobtained]. The intermediate X and the intermediate Y are caused to reactwith each other at 0 to 150° C. in the same manner as in the foregoing.Thus, the aromatic amine derivative represented by the general formula(7) can be synthesized. The number and kinds of substituents of Ar⁹ toAr¹³ can be changed by changing a starting material and a reactionintermediate. In addition, an aromatic amine derivative in which all ofAr⁹ to Ar¹³ each have a group represented by the general formula (1-2)or (1-1) can be synthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (8) is described.

An amine compound (such as commercially availableN,N′-diphenylbenzizine) is used as the intermediate X.

In addition, a halogen compound containing an amine compound includingthe general formula (1-2) and the general formula (1-1) is synthesizedas the intermediate Y in the same manner as in the foregoing [forexample, after acetamide and 4-(4-bromophenyl)-dibenzofuran have beencaused to react with each other at 1:1, 1 equivalent of2-(4-bromophenyl)-dibenzofuran is loaded and caused to react with thereaction product, followed by the hydrolysis of the resultant, and as aresult, the amine compound into which the general formula (1-1-3) andthe general formula (1-1-1) have been introduced is obtained. Further,the amine compound and 4′-iodobromobenzene are caused to react with eachother at 1:1, and as a result, the intermediate Y into which the generalformula (1-2) and the general formula (1-1) have been introduced isobtained]. The intermediate X and the intermediate Y are caused to reactwith each other at 0 to 150° C. in the same manner as in the foregoing.Thus, the aromatic amine derivative represented by the general formula(8) can be synthesized. The number and kinds of substituents of Ar¹⁴ toAr¹⁹ can be changed by changing a starting material and a reactionintermediate. In addition, an aromatic amine derivative in which all ofAr¹⁴ to Ar¹⁹ each have a group represented by the general formula (1-2)or (1-1) can be synthesized.

Next, a method of producing the aromatic amine derivative represented bythe general formula (9) is described.

An amine compound including the general formula (1-2) and the generalformula (1-1) is synthesized as the intermediate X in the same manner asin the foregoing [for example, after acetamide and4-(4-bromophenyl)-dibenzofuran have been caused to react with each otherat 1:1, 1 equivalent of 2-(4-bromophenyl)-dibenzofuran is loaded andcaused to react with the reaction product, followed by the hydrolysis ofthe resultant, and as a result, the intermediate X into which thegeneral formula (1-2) and the general formula (1-1) have been introducedis obtained].

An amino group-containing compound serving as a halide is used as theintermediate Y [such as commercially availabletris(4-bromophenyl)amine]. The intermediate X and the intermediate Y arecaused to react with each other at 0 to 150° C. in the same manner as inthe foregoing. Thus, the aromatic amine derivative represented by thegeneral formula (9) can be synthesized. The number and kinds ofsubstituents of Ar²⁰ to Ar²⁵ can be changed by changing a startingmaterial and a reaction intermediate. In addition, an aromatic aminederivative in which all of Ar²⁰ to Ar²⁵ each have a group represented bythe general formula (1-2) or (1-1) can be synthesized.

In addition, individual, similar synthesis methods described in knowntechnologies (JP 2003-171366 A, WO 2006/114921 A1, WO 2006/073054 A1, WO2007/125714 A1, and WO 2008/062636 A1) may each be employed for any suchsynthesis as described above.

Hereinafter, the structure of the organic EL device of the presentinvention is described.

Typical examples of the structure of the organic EL device of thepresent invention may include the following structures:

(1) anode/light emitting layer/cathode;

(2) anode/hole injecting layer/light emitting layer/cathode;

(3) anode/light emitting layer/electron injecting layer/cathode;

(4) anode/hole injecting layer/light emitting layer/electron injectinglayer/cathode;

(5) anode/organic semiconductor layer/light emitting layer/cathode;

(6) anode/organic semiconductor layer/electron barrier layer/lightemitting layer/cathode;

(7) anode/organic semiconductor layer/light emitting layer/adhesionimproving layer/cathode;

(8) anode/hole injecting layer/hole transporting layer/light emittinglayer/electron injecting layer/cathode;

(9) anode/insulating layer/light emitting layer/insulatinglayer/cathode;

(10) anode/inorganic semiconductor layer/insulating layer/light emittinglayer/insulating layer/cathode;

(11) anode/organic semiconductor layer/insulating layer/light emittinglayer/insulating layer/cathode;

(12) anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/insulating layer/cathode; and

(13) anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/electron injecting layer/cathode.

Of those, the structure (8) is preferably used in ordinary cases.However, the structure is not limited to the foregoing.

In addition, in the organic EL device of the present invention, thearomatic amine derivative represented by the general formula (1) of thepresent invention, which may be used in any layer of the above-mentionedorganic thin film layer, is preferably incorporated into a holeinjecting layer or a hole transporting layer. The content of thearomatic amine derivative represented by the general formula (1) isselected from 30 to 100 mol %.

The aromatic amine derivative of the present invention is preferablyused as a material for a hole injecting layer or hole transportinglayer.

The hole injecting layer and the hole transporting layer are layerswhich help injection of holes into the light emitting layer andtransport the holes to the light emitting region. The layer exhibits agreat mobility of holes and, in general, has an ionization energy assmall as 5.5 eV or less.

For such hole injecting layers and hole transporting layers, a materialwhich transports holes to the light emitting layer under an electricfield of a smaller strength is preferred. Further, a material whichexhibits, for example, a mobility of holes of at least 10⁻⁴ cm²/V·s ormore under application of an electric field of 10⁴ to 10⁶ V/cm ispreferred.

The aromatic amine derivative of the present invention is preferred as ahole transporting material because the derivative has small ionizationenergy and a large hole mobility. In addition, the aromatic aminederivative of the present invention is preferred as a hole injectingmaterial because of the following reasons. The derivative contains apolar group in any one of its molecules, and hence has good adhesivenesswith the anode and is hardly affected by, for example, a condition underwhich the substrate is washed. The organic EL device using the aromaticamine derivative of the present invention is expected to have alengthened lifetime by virtue of those factors.

The hole injecting layer or the hole transporting layer can be obtainedby forming a thin film from the aromatic amine derivative of the presentinvention in accordance with a known process such as a vacuum vapordeposition process, a spin coating process, a casting process, and an LBprocess. The thickness of the hole injecting layer or the holetransporting layer is not particularly limited. In general, thethickness is 5 nm to 5 μm.

The hole injecting layer or the hole transporting layer may be formed ofa single layer containing one or two or more kinds of theabove-mentioned aromatic amine derivatives, or may be a laminate formedof hole injecting layers or hole transporting layers containingdifferent kinds of compounds as long as the aromatic amine derivative ofthe present invention is incorporated in the hole transporting zone.

Further, an organic semiconductor layer is a layer for helping theinjection of holes and electrons into the light emitting layer. As theorganic semiconductor layer, a layer having a conductivity of 10⁻¹⁰ S/cmor more is preferred. As the material for the organic semiconductorlayer, the following can be used: oligomers containing thiophene;conductive oligomers such as oligomers containing arylamine; conductivedendrimers such as dendrimers containing arylamine; and the like.

The organic EL device is generally prepared on a substrate havinglight-transmissive property (light-transmissive substrate). Thelight-transmissive substrate is the substrate which supports the organicEL device. It is preferred that the light-transmissive substrate havetransmissive property which is a transmittance of light of 50% or morein the visible light region where the wavelength is 400 to 700 nm andstill preferably be flat and smooth.

Preferred examples of the light-transmissive substrate include glassplates and synthetic resin plates. Examples of the glass plate includeplates formed of soda-lime glass, glass containing barium and strontium,lead glass, aluminosilicate glass, borosilicate glass, bariumborosilicate glass, and quartz. Further, examples of the synthetic resinplate include plates formed of a polycarbonate resin, an acrylic resin,a polyethylene terephthalate resin, a polyether sulfide resin, and apolysulfone resin.

The anode has the function of injecting holes to the hole transportinglayer or the light emitting layer. It is effective that the anode has awork function of 4.5 eV or more. A material for the anode used in thepresent invention is specifically exemplified by indium tin oxide (ITO),a mixture of indium oxide and zinc oxide (IZO), a mixture of ITO andcerium oxide (ITCO), a mixture of IZO and cerium oxide (IZCO), a mixtureof indium oxide and cerium oxide (ICO), a mixture of zinc oxide andaluminum oxide (AZO), tin oxide (NESA), gold, silver, platinum, andcopper.

The anode may be obtained by forming a thin film with one of thematerials for electrodes by, for example, a vapor deposition process ora sputtering process.

As described above, when the light emitted from the light emitting layeris obtained through the anode, it is preferred that the anode have atransmittance of more than 10% with respect to the emitted light. It isalso preferred that the sheet resistance of the anode be several hundredΩ/cm or less. The thickness of the anode is, in general, selected in therange of 10 nm to 1 μm, preferably in the range of 10 to 200 nm althoughthe preferred range may be different depending on the used material.

As the cathode, a material such as a metal, an alloy, anelectroconductive compound, or a mixture of those materials, which havea small work function (4 eV or less) and are used as electrodematerials, is used. Specific examples of the electrode material includesodium, sodium-potassium alloys, magnesium, lithium, cesium,magnesium-silver alloys, aluminum/aluminum oxide, Al/Li₂O, Al/LiO,Al/LiF, aluminum-lithium alloys, indium, and rare earth metals.

The cathode can be obtained by forming a thin film of the electrodematerial described above in accordance with a process such as the vapordeposition process or the sputtering process.

Here, when the light emitted from the light emitting layer is obtainedthrough the cathode, it is preferred that the cathode have atransmittance of more than 10% with respect to the emitted light. It isalso preferred that the sheet resistivity of the cathode be severalhundred Ω/cm or less. The thickness of the cathode is generally 10 nm to1 μm, preferably 50 to 200 nm.

In general, defects in pixels tend to be formed inorganic EL devices dueto leak and short circuit because an electric field is applied toultra-thin films. In order to prevent the formation of the defects, aninsulating layer made of a thin film layer having insulating propertymay be inserted between the pair of electrodes. Examples of the materialused for the insulating layer include aluminum oxide, lithium fluoride,lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesiumfluoride, calcium oxide, calcium fluoride, aluminum nitride, titaniumoxide, silicon oxide, germanium oxide, silicon nitride, boron nitride,molybdenum oxide, ruthenium oxide, and vanadium oxide. Mixtures of twoor more kinds of the compounds and laminates formed of layers of two ormore kinds of the compounds may also be used as the insulating layer.

In the organic EL device of the present invention, the light emittinglayer has the following functions.

(i) The injecting function: the function of injecting holes from theanode or the hole injecting layer and injecting electrons from thecathode or the electron injecting layer when an electric field isapplied.

(ii) The transporting function: the function of transporting injectedcharges (i.e., electrons and holes) by the force of the electric field.

(iii) The light emitting function: the function of providing the fieldfor recombination of electrons and holes and leading the recombinationto the emission of light.

Examples of the process of forming the light emitting layer include aknown process such as a vapor deposition process, a spin coatingprocess, and an LB process. The light emitting layer is particularlypreferably a molecular deposit film. The term “molecular deposit film”as used here refers to a thin film formed by the deposition of amaterial compound in a vapor phase state, or a film formed by thesolidification of a material compound in a solution state or a liquidphase state. The molecular deposit film can be typically distinguishedfrom a thin film formed by the LB process (molecular accumulation film)on the basis of differences between the films in aggregation structureand higher order structure, and functional differences between the filmscaused by the foregoing differences.

In addition, the light emitting layer can also be formed by dissolving abinder such as a resin and a material compound into a solvent to therebyprepare a solution, and forming a thin film with the solution by thespin coating process or the like.

In the present invention, a light emitting material formed of apyrene-based derivative and an amine compound, or any other known metalcomplex compound may be incorporated into the light emitting layer.

The metal complex compound is preferably a metal complex compoundcontaining at least one metal selected from Ir, Ru, Pd, Pt, Os, and Re.The ligands of the complex preferably have at least one skeletonselected from a phenylpyridine skeleton, a bipyridyl skeleton, and aphenanthroline skeleton.

Specific examples of such metal complex compound includetris(2-phenylpyridine)iridium, tris(2-phenylpyridine)ruthenium,tris(2-phenylpyridine)palladium, bis(2-phenylpyridine)platinum,tris(2-phenylpyridine)osmium, tris(2-phenylpyridine)rhenium, octaethylplatinum porphyrin, octaphenyl platinum porphyrin, octaethyl palladiumporphyrin, and octaphenyl palladium porphyrin. However, the metalcomplex compound is not limited thereto. An appropriate metal complexcompound is selected in terms of a requested luminescent color, a deviceperformance, and a relationship with a host compound.

In addition, a phosphorescent dopant or a fluorescent dopant may be usedin the light emitting layer of the organic EL device of the presentinvention.

The phosphorescent dopant is a compound capable of emitting light from atriplet exciton. The dopant, which is not particularly limited as longas light is emitted from a triplet exciton, is preferably a metalcomplex containing at least one metal selected from the group consistingof Ir, Ru, Pd, Pt, Os, and Re, more preferably a porphyrin metal complexor an orthometalated metal complex. A porphyrin platinum complex ispreferred as the porphyrin metal complex. One kind of phosphorescentdopant may be used alone, or two or more kinds of phosphorescent dopantsmay be used in combination.

There are various ligands which can be used for forming anorthometalated metal complex. Preferred examples of the ligands include2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives,2-(2-thienyl)pyridine derivatives, 2-(1-naphthyl)pyridine derivatives,and 2-phenylquinoline derivatives. Each of those derivatives may have asubstituent as required. A fluorinated compound or the above-mentionedderivative having a trifluoromethyl group is particularly preferred as ablue-based dopant. The metal complex may further include a ligand otherthan the above-mentioned ligands such as acetylacetonato or picric acidas an auxiliary ligand.

The content of the phosphorescent dopant in the light emitting layer isnot particularly limited, and can be appropriately selected inaccordance with the purpose. The content is, for example, 0.1 to 70 mass%, more preferably 1 to 30 mass %. When the content of thephosphorescent dopant is less than 0.1 mass %, the intensity of emittedlight is weak, and an effect of the incorporation of the compound is notsufficiently exerted. When the content exceeds 70 mass %, a phenomenoncalled concentration quenching becomes remarkable, and deviceperformance reduces. Further, the light emitting layer may contain ahole transporting material, an electron transporting material, and apolymer binder as required.

Further, the light emitting layer has a thickness of preferably 5 to 50nm, more preferably 7 to 50 nm, most preferably 10 to 50 nm. When thethickness is less than 5 nm, the light emitting layer becomes difficultto form, and chromaticity may become difficult to adjust. When thethickness exceeds 50 nm, the voltage at which the device is driven mayincrease.

The fluorescent dopant is preferably a compound selected from, forexample, an amine-based compound, an aromatic compound, a chelatecomplex such as a tris(8-quinolinolato) aluminum complex, a coumarinderivative, a tetraphenylbutadiene derivative, a bisstyrylarylenederivative, and an oxadiazole derivative in accordance with a requestedluminescent color. An arylamine compound and an aryldiamine compound areparticularly preferred examples of such compound; out of thosecompounds, a styrylamine compound, a styryldiamine compound, an aromaticamine compound, or an aromatic diamine compound is more preferred, and afused polycyclic amine derivative is still more preferred. One kind ofthose fluorescent dopants may be used alone, or two or more kindsthereof may be used in combination.

The organic EL device of the present invention preferably contains atleast one of a styrylamine compound and an arylamine as the fluorescentdopant. A compound represented by the following general formula (50) ispreferably used as at least one of the styrylamine compound and thearylamine.

In the general formula (50), Ar₂₇ to Ar₂₉ each represent a substitutedor unsubstituted aromatic group having 6 to 40 ring carbon atoms, and urepresents an integer of 1 to 4, in particular, u preferably representsan integer of 1 or 2. One of Ar₂₇ to Ar₂₉ may represent a groupcontaining a styryl group. When one of Ar₂₇ and Ar₂₈ has a styryl group,at least one of Ar₂₈ and Ar₂₉ is preferably substituted with a styrylgroup.

Here, examples of the aromatic group having 6 to 40 ring carbon atomsinclude a phenyl group, a naphthyl group, an anthranyl group, aphenanthryl group, a pyrenyl group, a coronyl group, a biphenyl group, aterphenyl group, a pyrrolyl group, a furanyl group, a thiophenyl group,a benzothiophenyl group, an oxadiazolyl group, a diphenylanthranylgroup, an indolyl group, a carbazolyl group, a pyridyl group, abenzoquinolyl group, a fluoranthenyl group, an acenaphthofluoranthenylgroup, a stilbene group, a perylenyl group, a chrysenyl group, a picenylgroup, a triphenylenyl group, a rubicenyl group, a benzoanthracenylgroup, a phenylanthracenyl group, a bisanthracenyl group, and arylenegroups represented by the following general formulae (C) and (D). Ofthose, preferred are a naphthyl group, an anthranyl group, a chrysenylgroup, a pyrenyl group, and an arylene group represented by the generalformula (D).

In the general formula (C), r represents an integer of 1 to 3.

It should be noted that preferred examples of the substituent which issubstituted for the aryl group and arylene group include an alkyl grouphaving 1 to 6 carbon atoms (such as an ethyl group, a methyl group, ani-propyl group, an n-propyl group, an s-butyl group, a t-butyl group, apentyl group, a hexyl group, a cyclopentyl group, or a cyclohexylgroup), an alkoxy group having 1 to 6 carbon atoms (such as an ethoxygroup, a methoxy group, an i-propoxy group, an n-propoxy group, ans-butoxy group, a t-butoxy group, a pentoxy group, a hexyloxy group, acyclopentoxy group, or a cyclohexyloxy group), an aryl group having 5 to40 carbon atoms, an amino group substituted by an aryl group having 5 to40 carbon atoms, an ester group containing an aryl group having 5 to 40carbon atoms, an ester group containing an alkyl group having 1 to 6carbon atoms, a cyano group, a nitro group, and a halogen atom.

The light emitting material contained in the light emitting layer is notparticularly limited, and examples of the host materials includepolycyclic aromatic compounds such as an anthracene compound, aphenanthrene compound, a fluoranthene compound, a tetracene compound, atriphenylene compound, a chrysene compound, a pyrene compound, acoronene compound, a perylene compound, a phthaloperylene compound, anaphthaloperylene compound, a naphthacene compound, and a pentacenecompound, oxadiazole, bisbenzoxazoline, bisstyryl, cyclopentadiene, aquinoline metal complex, a tris(8-hydroxyquinolinato)aluminum complex, atris(4-methyl-8-quinolinato)aluminum complex, atris(5-phenyl-8-quinolinato)aluminum complex, an aminoquinoline metalcomplex, a benzoquinoline metal complex, tri-(p-terphenyl-4-yl)amine, a1-aryl-2,5-di(2-thienyl)pyrrole derivative, pyran, quinacridone,rubrene, a distyrylbenzene derivative, a distyrylarylene derivative, aporphyrin derivative, a stilbene derivative, a pyrazoline derivative, acoumarin-based dye, a pyran-based dye, a phthalocyanine-based dye, anaphthalocyanine-based dye, a croconium-based dye, a squalium-based dye,an oxobenzanthracene-based dye, a fluorescein-based dye, arhodamine-based dye, a pyrylium-based dye, a perylene-based dye, astilbene-based dye, a polythiophene-based dye, a rare-earthcomplex-based fluorescent substance, a rare-earth-based phosphorescentcomplex (such as an Ir complex), and polymer materials such asconductive polymers including polyvinylcarbazole, polysilane, andpolyethylenedioxidethiophene (PEDOT). Those compounds may be used alone,or a mixture of two or more kinds thereof may be used.

As the host material to be used in combination with the compounds of thepresent invention, compounds represented by the following formulae (11)to (17) are preferred.

An anthracene derivative represented by the following general formula(51).

In the general formula (51), A₂₁ and A₂₂ each independently represent asubstituted or unsubstituted aromatic cyclic group having 6 to 60 carbonatoms, and R₂₁ to R₂₈ each independently represent a hydrogen atom, asubstituted or unsubstituted aromatic cyclic group having 6 to 50 carbonatoms, a substituted or unsubstituted aromatic heterocyclic group having5 to 50 atoms, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 atoms, asubstituted or unsubstituted arylthio group having 5 to 50 atoms, asubstituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbonatoms, a substituted or unsubstituted silyl group, a carboxyl group, ahalogen atom, a cyano group, a nitro group, or a hydroxy group.

A pyrene derivative represented by the following general formula (52).

In the general formula (52), R₃₀ to R₃₉ each independently represent ahydrogen atom, a substituted or unsubstituted aromatic cyclic grouphaving 6 to 50 carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 5 to 50 atoms, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group, a substituted or unsubstituted alkoxy group having 1to 50 carbon atoms, a substituted or unsubstituted aralkyl group having6 to 50 carbon atoms, a substituted or unsubstituted aryloxy grouphaving 5 to 50 atoms, a substituted or unsubstituted arylthio grouphaving 5 to 50 atoms, a substituted or unsubstituted alkoxycarbonylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted silylgroup, a carboxyl group, a halogen atom, a cyano group, a nitro group,or a hydroxy group.

An anthracene derivative represented by the following general formula(53).

In the general formula (53), R₄₀ to R₄₉ each independently represent ahydrogen atom, an alkyl group, a cycloalkyl group, an aryl group whichmay be substituted, an alkoxyl group, an aryloxy group, an alkylaminogroup, an alkenyl group, an arylamino group, or a heterocyclic groupwhich may be substituted.

i and j each represent an integer of 1 to 5, and, when i or j represents2 or more, and R₄₀'s or R₄₁'s may be identical to or different from eachother. Further, R₄₀'s or R₄₁'s may be bonded to each other to form aring, and R₄₂ and R₄₃, R₄₄ and R₄₅, R₄₆ and R₄₇, or R₄₈ and R₄₉ may bebonded to each other to form a ring.

L₁ represents a single bond, —O—, —S—, —N(R)— (R represents an alkylgroup or an aryl group which may be substituted), an alkylene group, oran arylene group.

An anthracene derivative represented by the following general formula(54).

In the general formula (54), R₅₀ to R₅₉ each independently represent ahydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, analkoxyl group, an aryloxy group, an alkylamino group, an arylaminogroup, or a heterocyclic group which may be substituted.

k, l, m, and n each represent an integer of 1 to 5, and, when any one ofk, l, m, and n represents 2 or more, R₅₀'s, R₅₁'s, R₅₅'s, or R₅₆'s maybe identical to or different from each other. Further, R₅₂'s, R₅₃'s,R₅₄'s, or R₅₅'s may be bonded to each other to form a ring, and R₅₂ andR₅₃ or R₅₇ and R₅₈ may be bonded to each other to form a ring.

L₂ represents a single bond, —O—, —S—, —N(R)— (R represents an alkylgroup or an aryl group which may be substituted), an alkylene group, oran arylene group.

A spirofluorene derivative represented by the following general formula(55).

In the general formula (55), A₃₁ to A₃₄ each independently represent asubstituted or unsubstituted biphenylyl group, or a substituted orunsubstituted naphthyl group.

A compound represented by the following general formula (56).

In the general formula (56), Ar₄₁ to Ar₄₃ each independently represent asubstituted or unsubstituted arylene group having 6 to 60 carbon atoms,and Ar₄₄ to Ar₄₆ each independently represent a hydrogen atom, or asubstituted or unsubstituted aryl group having 6 to 60 carbon atoms.

R₆₁ to R₆₃ each independently represent a hydrogen atom, an alkyl grouphaving 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbonatoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxy grouphaving 5 to 18 carbon atoms, an aralkyloxy group having 7 to 18 carbonatoms, an aryl amino group having 5 to 16 carbon atoms, a nitro group, acyano group, an ester group having 1 to 6 carbon atoms, or a halogenatom.

A fluorene compound represented by the following general formula (57).

In the general formula (57), R₇₃ and R₇₄ each represent a hydrogen atom,a substituted or unsubstituted alkyl group, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heterocyclic group, a substituted aminogroup, a cyano group, or a halogen atom. R₇₁'s or R₇₂'s bonded todifferent fluorene groups may be identical to or different from eachother, and R₇₁ and R₇₂ bonded to the same fluorene group may beidentical to or different from each other.

R₉₃ and R₉₄ each represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group. R₇₃'s or R₇₄'s bonded to differentfluorene groups may be identical to or different from each other, andR₇₃ and R₇₄ bonded to the same fluorene group may be identical to ordifferent from each other.

Ar₇₁ and Ar₇₂ each represent a substituted or unsubstituted fusedpolycyclic aromatic group having three or more benzene rings in total,or a substituted or unsubstituted fused polycyclic heterocyclic groupthat has three or more rings each of which is a benzene ring or aheterocyclic ring in total and that is bonded to a fluorene group bycarbon. Ar₇₁ and Ar₇₂ may be identical to or different from each other.v represents an integer of 1 to 10.

Of the above-mentioned host materials, an anthracene derivative ispreferred, a monoanthracene derivative is more preferred, and anasymmetric anthracene is particularly preferred.

A host formed of a compound containing a carbazole ring and suitable forphosphorescence is a compound having a function of causing aphosphorescent compound to emit light as a result of the occurrence ofenergy transfer from the excited state of the host to the phosphorescentcompound. A host compound is not particularly limited as long as it is acompound capable of transferring exciton energy to a phosphorescentcompound, and can be appropriately selected in accordance with apurpose. The host compound may have, for example, an arbitraryheterocyclic ring in addition to a carbazole ring.

Specific examples of such host compound include a carbazole derivative,a triazole derivative, an oxazole derivative, an oxadiazole derivative,an imidazole derivative, a polyarylalkane derivative, a pyrazolinederivative, a pyrazolone derivative, a phenylenediamine derivative, anarylamine derivative, an amino-substituted chalcone derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an aromatictertiary amine compound, a styrylamine compound, an aromaticdimethylidene-based compound, a porphyrin-based compound, ananthraquinodimethane derivative, an anthrone derivative, adiphenylquinone derivative, a thiopyran dioxide derivative, acarbodiimide derivative, a fluorenylidenemethane derivative, adistyrylpyrazine derivative, a heterocyclic tetracarboxylic anhydridesuch as naphthaleneperylene, a phthalocyanine derivative, various metalcomplexes typified by a metal complex of an 8-quinolinol derivative anda metal complex having metal phthalocyanine, benzoxazole, orbenzothiazole as a ligand, and high molecular weight compounds such as apolysilane-based compound, a poly(N-vinylcarbazole) derivative, ananiline-based copolymer, a conductive high molecular weight oligomersuch as a thiophene oligomer or polythiophene, a polythiophenederivative, a polyphenylene derivative, a polyphenylene vinylenederivative, and a polyfluorene derivative. One kind of the hostcompounds may be used alone, or two or more kinds thereof may be used incombination.

Specific examples of the compounds include the following compounds.

Next, each of the electron injecting layer and the electron transportinglayer is a layer which helps injection of electrons into the lightemitting layer, transports the electrons to the light emitting region,and exhibits a great mobility of electrons. Further, the adhesionimproving layer is an electron injecting layer including a materialexhibiting particularly improved adhesion with the cathode.

In addition, it is known that, in an organic EL device, emitted light isreflected by an electrode (cathode in this case), and hence emittedlight directly extracted from an anode and emitted light extracted viathe reflection by the electrode interfere with each other. The thicknessof an electron transporting layer is appropriately selected from therange of several nanometers to several micrometers in order that theinterference effect may be effectively utilized. In particular, when thethickness of the electron transporting layer is large, an electronmobility is preferably at least 10⁻⁶ cm²/V·s or more upon application ofan electric field of 10⁴ to 10⁶ V/cm in order to avoid an increase involtage.

A metal complex of 8-hydroxyquinoline or of a derivative of8-hydroxyquinoline, or an oxadiazole derivative is suitable as amaterial to be used in an electron injecting layer. Specific examples ofthe above-mentioned metal complex of 8-hydroxyquinoline or of thederivative of 8-hydroxyquinoline that can be used as an electroninjecting material include metal chelate oxynoid compounds eachcontaining a chelate of oxine (generally 8-quinolinol or8-hydroxyquinoline), such as tris(8-quinolinol)aluminum.

On the other hand, examples of the oxadiazole derivative includeelectron transfer compounds represented by the following generalformulae.

In the formulae: Ar₈₁, Ar₈₂, Ar₈₃, Ar₈₅, Ar₈₆, and Ar₈₉ each represent asubstituted or unsubstituted aryl group and may be identical to ordifferent from each other. Further, Ar₈₄, Ar₈₇, and Ar₈₈ each representa substituted or unsubstituted arylene group and may be identical to ordifferent from each other.

Examples of the aryl group include a phenyl group, a biphenylyl group,an anthryl group, a perylenyl group, and a pyrenyl group. Further,examples of the arylene group include a phenylene group, a naphthylenegroup, a biphenylylene group, an anthrylene group, a perylenylene group,and a pyrenylene group. In addition, examples of the substituent includean alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to10 carbon atoms, and a cyano group. As the electron transfer compound, acompound which can form a thin film is preferred.

The hole injecting layer and the hole transporting layer are layerswhich help injection of holes into the light emitting layer andtransports the holes to the light emitting region. The layers eachexhibit a great mobility of holes and, in general, have an ionizationenergy as small as 5.5 eV or less.

As such hole injecting layer and hole transporting layer, a materialwhich transports holes to the light emitting layer under an electricfield of a smaller strength is preferred. A material which exhibits, forexample, a mobility of holes of at least 10⁻⁴ cm²/V·sec underapplication of an electric field of 10⁴ to 10⁶ V/cm is preferred.

When the aromatic amine derivative of the present invention is used inthe hole transporting zone, the aromatic amine derivative of the presentinvention may be used alone or as a mixture with other materials forforming the hole injecting layer or the hole transporting layer.

The material which can be used as a mixture with the aromatic aminederivative of the present invention for forming the hole injecting layerand the hole transporting layer is not particularly limited as long asthe material has the preferred property. The material can be arbitrarilyselected from materials which are conventionally used as the chargetransporting material of holes in photoconductive materials and knownmaterials which are used for the hole injecting layer and the holetransporting layer in organic EL devices. In the present invention, amaterial which has a hole transporting ability and which can be used ina hole transporting zone is referred to as “hole transporting material”.

Examples of the aromatic amine derivative to be used in each of the holeinjecting layer and the hole transporting layer include compoundsrepresented by the following formula.

Ar₂₁₁ to Ar₂₁₃, Ar₂₂₁ to Ar₂₂₃, and Ar₂₀₃ to Ar₂₀₈ each represent asubstituted or unsubstituted aromatic hydrocarbon group having 6 to 50carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup having 5 to 50 atoms, and p, q, s, t, w, and y each represent aninteger of 0 to 3.

Specific examples of the substituted or unsubstituted aromatichydrocarbon group having 6 to 50 carbon atoms include a phenyl group, a1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrylgroup, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group,a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group.

Specific examples of the substituted or unsubstituted aromaticheterocyclic group having 5 to 50 atoms include a 1-pyrrolyl group, a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinylgroup, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolylgroup, a 6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a2-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a2-furyl group, a 3-furyl group, a 2-benzofuryl group, a 3-benzofurylgroup, a 4-benzofuryl group, a 5-benzofuryl group, a 6-benzofuryl group,a 7-benzofuryl group, a 1-isobenzofuryl group, a 3-isobenzofuryl group,a 4-isobenzofuryl group, a 5-isobenzofuryl group, a 6-isobenzofurylgroup, a 7-isobenzofuryl group, a quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinylgroup, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a7-phenanthridinyl group, an 8-phenanthridinyl group, a 9-phenanthridinylgroup, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinylgroup, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a1,7-phenanthrolin-2-yl group, a 1,7-phenanthrolin-3-yl group, a1,7-phenanthrolin-4-yl group, a 1,7-phenanthrolin-5-yl group, a1,7-phenanthrolin-6-yl group, a 1,7-phenanthrolin-8-yl group, a1,7-phenanthrolin-9-yl group, a 1,7-phenanthrolin-10-yl group, a1,8-phenanthrolin-2-yl group, a 1,8-phenanthrolin-3-yl group, a1,8-phenanthrolin-4-yl group, a 1,8-phenanthrolin-5-yl group, a1,8-phenanthrolin-6-yl group, a 1,8-phenanthrolin-7-yl group, a1,8-phenanthrolin-9-yl group, a 1,8-phenanthrolin-10-yl group, a1,9-phenanthrolin-2-yl group, a 1,9-phenanthrolin-3-yl group, a1,9-phenanthrolin-4-yl group, a 1,9-phenanthrolin-5-yl group, a1,9-phenanthrolin-6-yl group, a 1,9-phenanthrolin-7-yl group, a1,9-phenanthrolin-8-yl group, a 1,9-phenanthrolin-10-yl group, a1,10-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group, a1,10-phenanthrolin-4-yl group, a 1,10-phenanthrolin-5-yl group, a2,9-phenanthrolin-1-yl group, a 2,9-phenanthrolin-3-yl group, a2,9-phenanthrolin-4-yl group, a 2,9-phenanthrolin-5-yl group, a2,9-phenanthrolin-6-yl group, a 2,9-phenanthrolin-7-yl group, a2,9-phenanthrolin-8-yl group, a 2,9-phenanthrolin-10-yl group, a2,8-phenanthrolin-1-yl group, a 2,8-phenanthrolin-3-yl group, a2,8-phenanthrolin-4-yl group, a 2,8-phenanthrolin-5-yl group, a2,8-phenanthrolin-6-yl group, a 2,8-phenanthrolin-7-yl group, a2,8-phenanthrolin-9-yl group, a 2,8-phenanthrolin-10-yl group, a2,7-phenanthrolin-1-yl group, a 2,7-phenanthrolin-3-yl group, a2,7-phenanthrolin-4-yl group, a 2,7-phenanthrolin-5-yl group, a2,7-phenanthrolin-6-yl group, a 2,7-phenanthrolin-8-yl group, a2,7-phenanthrolin-9-yl group, a 2,7-phenanthrolin-10-yl group, a1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinylgroup, a 10-phenothiazinyl group, a 1-phenoxazinyl group, a2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinyl group, a10-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl1-indolyl group, a 4-t-butyl1-indolyl group, a2-t-butyl3-indolyl group, and a 4-t-butyl3-indolyl group.

Further, a compound represented by the following formula can be used ineach of the hole injecting layer and the hole transporting layer.

Ar₂₃₁ to Ar₂₃₄ each represent a substituted or unsubstituted aromatichydrocarbon group having 6 to 50 carbon atoms, or a substituted orunsubstituted aromatic heterocyclic group having 5 to 50 atoms.

L is a linking group and represents a single bond, a substituted orunsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, ora substituted or unsubstituted aromatic heterocyclic group having 5 to50 atoms, and x represents an integer of 0 to 5.

Here, specific examples of the substituted or unsubstituted aromatichydrocarbon group having 6 to 50 carbon atoms, and the substituted orunsubstituted aromatic heterocyclic group having 5 to 50 atoms includethe same examples as those described above.

Further, specific examples of the materials for the hole injecting layerand the hole transporting layer include a triazole derivative, anoxadiazole derivative, an imidazole derivative, a polyarylalkanederivative, a pyrazoline derivative, and a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, an oxazole derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, apolysilane-based copolymer, an aniline-based copolymer, and a conductivehigh molecular weight oligomer (in particular, a thiophene oligomer).

The above-mentioned materials may be used as the materials for the holeinjecting layer and the hole transporting layer, and it is preferred touse a porphyrin compound, an aromatic tertiary amine compound, and astyrylamine compound. It is particularly preferred to use an aromatictertiary amine compound.

Further, there may be given a compound having two fused aromatic ringsin any one of its molecules such as4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter abbreviatedas “NPD”), 4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine(hereinafter abbreviated as “MTDATA”) in which three triphenylamineunits are linked to each other in a starburst pattern, and the like.

In addition to the foregoing, a nitrogen-containing heterocyclicderivative represented by the following formula can be used.

In the above-mentioned formula, R₁₂₁ to R₁₂₆ each represent any one of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, a substituted or unsubstituted aralkyl group, and asubstituted or unsubstituted heterocyclic group, provided that R₁₂₁ toR₁₂₆ may be identical to or different from one another, and R₁₂₁ andR₁₂₂, R₁₂₃ and R₁₂₄, R₁₂₅ and R₁₂₆, R₁₂₁ and R₁₂₆, R₁₂₂ and R₁₂₃, orR₁₂₄ and R₁₂₅ may form a fused ring.

Further, a compound represented by the following formula can be used.

In the above-mentioned formula, R₁₃₁ to R₁₃₆ each represent asubstituent, preferably an electron-withdrawing group such as a cyanogroup, a nitro group, a sulfonyl group, a carbonyl group, atrifluoromethyl group, or a halogen.

As typified by those materials, acceptor materials can each also be usedas the hole injecting material. Specific examples of the materials areas described above.

Further, in addition to the aromatic dimethylidyne-based compoundsdescribed above as the material for the light emitting layer, inorganiccompounds such as Si of the p-type and SiC of the p-type can also beused as the material for the hole injecting layer and the holetransporting layer.

The hole injecting layer and the hole transporting layer can be obtainedby forming a thin film from the aromatic amine derivative of the presentinvention in accordance with a known process such as the vacuum vapordeposition process, the spin coating process, the casting process, andthe LB process.

The thickness of each of the hole injecting layer and the holetransporting layer is not particularly limited. In general, thethickness is 5 nm to 5 μm. The hole injecting layer and the holetransporting layer may be formed of a single layer containing one kindor two or more kinds of materials described above or may be a laminateformed of a hole injecting layer and a hole transporting layercontaining different kinds of compounds as long as the aromatic aminederivative of the present invention is incorporated in the holetransporting zone.

Further, an organic semiconductor layer may be formed as a layer forhelping the injection of holes into the light emitting layer. A layerhaving a conductivity of 10⁻¹⁰ S/cm or more is preferred. As a materialfor the organic semiconductor layer, there may be used as conductiveoligomers such as oligomers containing thiophene and oligomerscontaining arylamine, conductive dendrimers such as dendrimerscontaining arylamine, and the like.

As for a method of producing the organic EL device of the presentinvention, the anode, light emitting layer, hole injecting layer, andelectron injecting layer may be formed in accordance with theabove-mentioned process using the materials, and the cathode may beformed in the last step. Further, the organic EL device may also beproduced by forming the above-mentioned layers in the order reverse tothe order described above, i.e., the cathode being formed in the firststep and the anode in the last step.

Hereinafter, an example of producing an organic EL device having aconfiguration in which an anode, a hole injecting layer, a lightemitting layer, an electron injecting layer, and a cathode are formedsuccessively on a light-transmissive substrate is described.

First, on a suitable light-transmissive substrate, a thin film made of amaterial for the anode is formed in accordance with the vapor depositionprocess or the sputtering process so that the thickness of the formedthin film is 1 μm or less, preferably in the range of 10 to 200 nm. Theformed thin film is used as the anode.

Then, a hole injecting layer is formed on the anode. The hole injectinglayer can be formed in accordance with the vacuum vapor depositionprocess, the spin coating process, the casting process, the LB process,or the like, as described above. The vacuum vapor deposition process ispreferred because a uniform film can be easily obtained and thepossibility of formation of pin holes is small.

When the hole injecting layer is formed in accordance with the vacuumvapor deposition process, in general, it is preferred that theconditions be suitably selected from the following ranges: thetemperature of the source of the deposition: 50 to 450° C.; the degreeof vacuum: 10⁻⁷ to 10⁻³ Torr; the rate of deposition: 0.01 to 50 nm/s;the temperature of the substrate: −50 to 300° C.; and the thickness ofthe film: 5 nm to 5 μm, although the conditions of the vacuum vapordeposition are different depending on the compound to be used (materialfor the hole injecting layer) and the crystal structure and therecombination structure of the target hole injecting layer.

Then, the light emitting layer is formed on the hole injecting layer.The formation of the light emitting layer can be achieved by forming athin film of the light emitting material using the light emittingmaterial according to the present invention in accordance with a processsuch as the vacuum vapor deposition process, the sputtering process, thespin coating process, or the casting process. The vacuum vapordeposition process is preferred because a uniform film can be easilyobtained and the possibility of formation of pin holes is small.

When the light emitting layer is formed in accordance with the vacuumvapor deposition process, in general, the conditions of the vapordeposition process can be selected from the same condition ranges asthose for the formation of the hole injecting layer, although theconditions are different depending on the compound to be used. Thethickness is preferably within the range of 10 to 40 nm.

Next, an electron injecting layer is formed on the light emitting layer.In this case, similarly to the hole injecting layer and the lightemitting layer, it is preferred that the electron injecting layer beformed in accordance with the vacuum vapor deposition process because auniform film is requested to be obtained. The conditions of the vapordeposition can be selected from the same condition ranges as those forthe hole injecting layer and the light emitting layer.

After that, a cathode is laminated, and an organic EL device can beobtained. The cathode is formed of a metal and can be formed inaccordance with the vapor deposition process, the sputtering process, orthe like. It is preferred that the vacuum vapor deposition process beused in view of preventing damages of the lower organic thin film layersduring the formation of the film.

In the production of the organic EL device as describe above, it ispreferred that the layers from the anode to the cathode be formedsuccessively by vacuuming once.

The method of forming the respective layers in the organic EL device ofthe present invention is not particularly limited. A conventionallyknown process such as the vacuum vapor deposition process or the spincoating process can be used. The organic thin film layer which is usedin the organic EL device of the present invention and includes thecompound represented by the general formula (1) can be formed inaccordance with a known process such as the vacuum vapor depositionprocess, the molecular beam epitaxy process (MBE process), or a coatingprocess such as the dipping process, the spin coating process, thecasting process, the bar coating process, or the roll coating processusing a solution prepared by dissolving the compounds into a solvent.

The thickness of each organic thin film layer in the organic EL deviceof the present invention is not particularly limited. However, athickness in the range of several nanometers to 1 μm is preferred inorder to prevent defects such as pin holes and to improve efficiency.

It should be noted that, in a case of applying a direct voltage to theorganic EL device, emitted light can be observed, when a direct voltageof 5 to 40 V is applied in the condition that the polarity of the anodeis plus (+) and the polarity of the cathode is minus (−). In addition,when the polarities are reversed and an electric voltage is applied, noelectric current flows and no light is emitted at all. Further, when analternating voltage is applied, a uniform emitted light can be observedonly in the condition that the polarity of the anode is plus (+) and thepolarity of the cathode is minus (−). When an alternating voltage isapplied, any type of wave shape can be used.

The organic EL device of the present invention can find use in: flatluminous bodies for the flat panel displays of wall-hung televisions andthe like; light sources for the backlights, measuring gauges, and thelike of copying machines, printers, and liquid crystal displays; displayboards; and marker lamps. In addition, the material of the presentinvention can be used not only in an organic EL device but also in thefields of, for example, an electrophotographic photosensitive member, aphotoelectric converter, a solar cell, and an image sensor.

EXAMPLES Synthesis Example 1-1 Synthesis of Intermediate 1-1

In a stream of argon, to a 1,000-mL three-necked flask, 47 g of4-bromobiphenyl, 23 g of iodine, 9.4 g of periodic acid dihydrate, 42 mLof water, 360 mL of acetic acid, and 11 mL of sulfuric acid werecharged, and the mixture was stirred at 65° C. for 30 minutes and wasthen subjected to a reaction at 90° C. for 6 hours. The reactant waspoured into ice water, followed by filtering. The resultant was washedwith water, and then washed with methanol, whereby 67 g of a whitepowder were obtained. Main peaks having ratios m/z of 358 and 360 wereobtained with respect to C₁₂H₈BrI=359 by a field desorption massspectrometry (hereinafter, FD-MS) analysis, so the powder was identifiedas Intermediate 1-1.

Synthesis Example 1-2 Synthesis of Intermediate 1-2

A reaction was performed in the same manner as in Synthesis Example 1-1except that 2-bromo-9,9-dimethylfluorene was used instead of4-bromobiphenyl. As a result, 61 g of a white powder were obtained. Thepowder was identified as Intermediate 1-2 by FD-MS analysis because mainpeaks having ratios m/z of 398 and 400 were obtained with respect toC₁₅H₁₂BrI=399.

Synthesis Example 1-3 Synthesis of Intermediate 1-3

150 grams (892 mmol) of dibenzofuran and 1 L of acetic acid were loadedinto a flask. The air in the flask was replaced with nitrogen, and thenthe contents were dissolved under heat. 188 grams (1.18 mol) of brominewere dropped to the solution while the flask was sometimes cooled withwater. After that, the mixture was stirred for 20 hours under aircooling. The precipitated crystal was separated by filtration, and wasthen sequentially washed with acetic acid and water. The washed crystalwas dried under reduced pressure. The resultant crystal was purified bydistillation under reduced pressure, and was then repeatedlyrecrystallized with methanol several times. Thus, 66.8 g of2-bromodibenzofuran were obtained (in 31% yield). The resultant wasidentified as Intermediate 1-3 by FD-MS analysis.

Synthesis Example 1-4 Synthesis of Intermediate 1-4

Under an argon atmosphere, 400 mL of anhydrous THF were added to 24.7 g(100 mmol) of 2-bromodibenzofuran (Intermediate 1-3), and then 63 mL(100 mmol) of a solution of n-butyllithium in hexane having aconcentration of 1.6 M were added to the mixture during the stirring ofthe mixture at −40° C. The reaction solution was stirred for 1 hourwhile being heated to 0° C. The reaction solution was cooled to −78° C.again, and then a solution of 26.0 g (250 mmol) of trimethyl borate in50 mL of dry THF was dropped to the solution. The reaction solution wasstirred at room temperature for 5 hours. 200 milliliters of 1Nhydrochloric acid were added to the solution, and then the mixture wasstirred for 1 hour. After that, the aqueous layer was removed. Theorganic layer was dried with magnesium sulfate, and then the solvent wasremoved by distillation under reduced pressure. The resultant solid waswashed with toluene. Thus, 15.2 g of dibenzofuran-2-boronic acid wereobtained (in 72% yield). The resultant was identified as Intermediate1-4 by FD-MS analysis because a main peak having a ratio m/z of 212 wasobtained with respect to C₁₂H₉BO₃=212.

Synthesis Example 1-5 Synthesis of Intermediate 1-5

Under an argon atmosphere, 300 mL of toluene and 150 mL of an aqueoussolution of sodium carbonate having a concentration of 2 M were added to28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) ofdibenzofuran-2-boronic acid (Intermediate 1-4), and 2.31 g (2.00 mmol)of tetrakis(triphenylphosphine) palladium(0), and then the mixture washeated while being refluxed for 10 hours.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 26.2 g of a whitecrystal of 4-(4-bromophenyl)dibenzofuran were obtained (in 81% yield).The crystal was identified as Intermediate 1-5 by FD-MS analysis.

Synthesis Example 1-6 Synthesis of Intermediate 1-6

A reaction was performed in the same manner as in Synthesis Example 1-5except that 22.3 g of dibenzofuran-4-boronic acid were used instead ofdibenzofuran-2-boronic acid. As a result, 23.1 g of a white powder wereobtained. The powder was identified as Intermediate 1-6 by FD-MSanalysis.

Synthesis Example 1-7 Synthesis of Intermediate 1-7

A reaction was performed in the same manner as in Synthesis Example 1-6except that 36 g of Intermediate 1-1 were used instead of4-iodobromobenzene. As a result, 28.1 g of a white powder were obtained.The powder was identified as Intermediate 1-6 by FD-MS analysis.

Synthesis Example 1-8 Synthesis of Intermediate 1-8

A reaction was performed in the same manner as in Synthesis Example 1-6except that 40 g of Intermediate 1-2 were used instead of4-iodobromobenzene. As a result, 30.2 g of a white powder were obtained.The powder was identified as Intermediate 1-8 by FD-MS analysis.

Synthesis Example 1-9 Synthesis of Intermediate 1-9

Under an argon atmosphere, 2 mL of trans-1,2-cyclohexanediamine and 300mL of 1,4-dioxane were added to 28.3 g (100 mmol) of 4-iodobromobenzene,16.7 g (100 mmol) of carbazole, 0.2 g (1.00 mmol) of copper iodide(CuI), and 42.4 g (210 mmol) of tripotassium phosphate, and then themixture was stirred at 100° C. for 20 hours.

After the completion of the reaction, 300 mL of water were added to theresultant. After that, the mixture was subjected to liquid separation,and then the aqueous layer was removed. The organic layer was dried withsodium sulfate, and was then concentrated. The residue was purified bysilica gel column chromatography. Thus, 18.3 g of a white crystal wereobtained (in 57% yield). The resultant was identified as Intermediate1-9 by FD-MS analysis.

Synthesis Example 1-10 Synthesis of Intermediate 1-10

A reaction was performed in the same manner as in Synthesis Example 1-9except that 36 g of Intermediate 1-1 were used instead of4-iodobromobenzene. As a result, 23.1 g of a white powder were obtained.The powder was identified as Intermediate 1-10 by FD-MS analysis.

Synthesis Example 1-11 Synthesis of Intermediate 1-11

In a stream of argon, 670 g of carbazole, 850 kg of iodobenzene, 20 L ofxylene, 460 g of t-BuONa, and palladium acetate (Pd(OAc)₂) were loaded,and then the mixture was refluxed for 8 hours. Impurities werefiltrated, and then the filtrate was concentrated under reduced pressureand washed with hexane. After that, the washed product was dried. As aresult, 820 g of phenylcarbazole were obtained as a white powder. Areaction was performed in the same manner as in the synthesis ofIntermediate 1-1 except that phenylcarbazole was used instead of4-bromobiphenyl. As a result, 650 g of a white powder were obtained. Thepowder was identified as Intermediate 1-11 by FD-MS analysis.

Synthesis Example 1-12 Synthesis of Intermediate 1-12

A reaction was performed in the same manner as in Synthesis Examples 1-4and 1-5 except that Intermediate 1-11 was used instead of Intermediate1-3. As a result, 250 g of a white powder were obtained. The powder wasidentified as Intermediate 1-12 by FD-MS analysis.

Synthesis Example 1-13 Synthesis of Intermediate 1-13

In a stream of argon, 16.8 g of diphenylamine, 36.0 g of Intermediate1-1, 10 g of t-butoxy sodium (manufactured by Hiroshima Wako Ltd.), 1.6g of bis(triphenylphosphine) palladium (II) chloride (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded andsubjected to a reaction at 130° C. for 24 hours.

After the resultant had been cooled, 1,000 mL of water were added to theresultant, and then the mixture was filtrated with celite. The filtratewas extracted with toluene, and was then dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure. Theresultant coarse product was subjected to column purification, and wasthen recrystallized with toluene. The crystal was taken by filtration,and was then dried. As a result, 12.4 g of a pale yellow powder wereobtained. The powder was identified as Intermediate 1-13 by FD-MSanalysis.

Synthesis Example 1-14 Synthesis of Intermediate 1-14

A reaction was performed in the same manner as in Synthesis Example 1-13except that 4-iodobromobenzene was used instead of Intermediate 1-1. Asa result, 9.3 g of a white powder were obtained. The powder wasidentified as Intermediate 1-14 by FD-MS analysis.

Synthesis Example 1-15 Synthesis of Intermediate 1-15

In a stream of argon, 185 g of 1-acetamide (manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), 323 g of Intermediate 1-6 (manufactured byWako Pure Chemical Industries, Ltd.), 544 g of potassium carbonate(manufactured by Wako Pure Chemical Industries, Ltd.), 12.5 g of acopper powder (manufactured by Wako Pure Chemical Industries, Ltd.), and2 L of decalin were loaded and subjected to a reaction at 190° C. for 4days. After the reaction, the resultant was cooled, and then 2 L oftoluene were added to the resultant. The insoluble portion was taken byfiltration. The product taken by filtration was dissolved in 4.5 L ofchloroform, and then the insoluble portion was removed. After that, theremainder was subjected to an activated carbon treatment andconcentrated. 3 liters of acetone were added to the resultant, and then181 g of the precipitated crystal were taken by filtration. The crystalwas identified as Intermediate 1-15 by FD-MS analysis.

Synthesis Example 1-16 Synthesis of Intermediate 1-16

In a stream of argon, Intermediate 1-15 was suspended in 5 L of ethyleneglycol (manufactured by Wako Pure Chemical Industries, Ltd.) and 50 mLof water, and then 210 g of an 85% aqueous solution of potassiumhydroxide were added to the suspension. After that, the mixture wassubjected to a reaction at 120° C. for 8 hours. After the reaction, thereaction liquid was injected into 10 L of water, and then theprecipitated crystal was taken by filtration. The crystal was washedwith water and methanol. The resultant crystal was dissolved in 3 L oftetrahydrofuran under heat. The solution was subjected to an activatedcarbon treatment, and was then concentrated. Acetone was added to theresultant to precipitate a crystal. The crystal was taken by filtration.Thus, 151 g of a white powder were obtained. The powder was identifiedas Intermediate 1-16 by FD-MS analysis.

Synthesis Example 1-17 Synthesis of Intermediate 1-17

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that Intermediate 1-7 was used instead ofIntermediate 1-6. As a result, 172 g of a white powder were obtained.The powder was identified as Intermediate 1-17 by FD-MS analysis.

Synthesis Example 1-18 Synthesis of Intermediate 1-18

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that Intermediate 1-8 was used instead ofIntermediate 1-6. As a result, 168 g of a white powder were obtained.The powder was identified as Intermediate 1-18 by FD-MS analysis.

Synthesis Example 1-19 Synthesis of Intermediate 1-19

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that Intermediate 1-5 was used instead ofIntermediate 1-6. As a result, 153 g of a white powder were obtained.The powder was identified as Intermediate 1-19 by FD-MS analysis.

Synthesis Example 1-20 Synthesis of Intermediate 1-20

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that the usage of Intermediate 1-6 was changed from323 g to 678 g. As a result, 280 g of a white powder were obtained. Thepowder was identified as Intermediate 1-20 by FD-MS analysis.

Synthesis Example 1-21 Synthesis of Intermediate 1-21

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: Intermediate 1-15 was used instead of1-acetamide; and 4-bromo-p-terphenyl was used instead of Intermediate1-6. As a result, 280 g of a white powder were obtained. The powder wasidentified as Intermediate 1-21 by FD-MS analysis.

Synthesis Example 1-22 Synthesis of Intermediate 1-22

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that Intermediate 1-5 was used instead ofIntermediate 1-6. As a result, 245 g of a white powder were obtained.The powder was identified as Intermediate 1-22 by FD-MS analysis.

Synthesis Example 1-23 Synthesis of Intermediate 1-23

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: Intermediate 1-15 was used instead of1-acetamide; and Intermediate 1-9 was used instead of Intermediate 1-6.As a result, 255 g of a white powder were obtained. The powder wasidentified as Intermediate 1-23 by FD-MS analysis.

Synthesis Example 1-24 Synthesis of Intermediate 1-24

In a stream of argon, 11.0 g of aniline, 32.3 g of Intermediate 1-9,13.6 g of t-butoxy sodium (manufactured by Hiroshima Wako Ltd.), 0.92 gof tris(dibenzylideneacetone)dipalladium(0) (manufactured by SigmaAldrich Co.), and 600 mL of dry toluene were loaded and subjected to areaction at 80° C. for 8 hours.

After the resultant had been cooled, 500 mL of water were added to theresultant, and then the mixture was filtrated with celite. The filtratewas extracted with toluene, and was then dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure. Theresultant coarse product was subjected to column purification, and wasthen recrystallized with toluene. The crystal was taken by filtration,and was then dried. As a result, 23.8 g of an amine derivative (paleyellow powder) were obtained. Further, a reaction was performed in thesame manner as in Synthesis Example 1-13 except that the aminederivative (pale yellow powder) obtained in the foregoing was usedinstead of diphenylamine. As a result, 28.4 g of a white powder wereobtained. The powder was identified as Intermediate 1-24 by FD-MSanalysis.

Synthesis Example 1-25 Synthesis of Intermediate 1-25

A reaction was performed in the same manner as in Synthesis Example 1-24except that 4-iodobromobenzene was used instead of Intermediate 1-1 inthe reaction on the second stage. As a result, 22.5 g of an amineintermediate (white powder) were obtained. Further, a reaction wasperformed in the same manner as in Synthesis Example 1-13 except thatthe amine intermediate (white powder) obtained in the foregoing was usedinstead of diphenylamine. As a result, 23.4 g of a white powder wereobtained. The powder was identified as Intermediate 1-25 by FD-MSanalysis.

Synthesis Example 1-26 Synthesis of Intermediate 1-26

In a stream of argon, 185 g of 1-acetamide (manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), 323 g of Intermediate 1-6 (manufactured byWako Pure Chemical Industries, Ltd.), 544 g of potassium carbonate(manufactured by Wako Pure Chemical Industries, Ltd.), 12.5 g of acopper powder (manufactured by Wako Pure Chemical Industries, Ltd.), and2 L of decalin were loaded and subjected to a reaction at 190° C. for 4days. After the reaction, the resultant was cooled, and then 2 L oftoluene were added to the resultant. The insoluble portion was taken byfiltration. The product taken by filtration was dissolved in 4.5 L ofchloroform, and then the insoluble portion was removed. After that, theremainder was subjected to an activated carbon treatment andconcentrated. 3 liters of acetone were added to the resultant, and then175 g of the precipitated crystal were taken by filtration.

To the resultant, 120 g of 4,4′-diiodobiphenyl (manufactured by WakoPure Chemical Industries, Ltd.), 163 g of potassium carbonate(manufactured by Wako Pure Chemical Industries, Ltd.), 3.8 g of a copperpowder (manufactured by Wako Pure Chemical Industries, Ltd.), and 600 mLof decalin were loaded and subjected to a reaction at 190° C. for 4days.

After the reaction, the resultant was cooled, and then 600 mL of toluenewere added to the resultant. The insoluble portion was taken byfiltration. The product taken by filtration was dissolved in 1.4 L ofchloroform, and then the insoluble portion was removed. After that, theremainder was subjected to an activated carbon treatment andconcentrated. 1 liter of acetone were added to the resultant, and then391 g of the precipitated crystal were taken by filtration.

The resultant was suspended in 1.5 L of ethylene glycol (manufactured byWako Pure Chemical Industries, Ltd.) and 15 mL of water, and then 44 gof an 85% aqueous solution of potassium hydroxide were added to thesuspension. After that, the mixture was subjected to a reaction at 120°C. for 8 hours. After the reaction, the reaction liquid was injectedinto 10 L of water, and then the precipitated crystal was taken byfiltration. The crystal was washed with water and methanol. Theresultant crystal was dissolved in 1 L of tetrahydrofuran under heat.The solution was subjected to an activated carbon treatment, and wasthen concentrated. Acetone was added to the resultant to precipitate acrystal. The crystal was taken by filtration. Thus, 140 g of a whitepowder were obtained. The powder was identified as Intermediate 1-26 byFD-MS analysis.

Synthesis Example 1-27 Synthesis of Intermediate 1-27

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that Intermediate 1-9 was used instead ofIntermediate 1-6. As a result, 221 g of a white powder were obtained.The powder was identified as Intermediate 1-27 by FD-MS analysis.

Synthesis Example 1-28 Synthesis of Intermediate 1-28

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except the following. After 323 g of Intermediate 1-6 hadbeen subjected to a reaction, 323 g of Intermediate 1-5 were added tothe reaction liquid, and then the mixture was continuously subjected toa reaction. As a result, 232 g of a white powder were obtained. Thepowder was identified as Intermediate 1-28 by FD-MS analysis.

Synthesis Example 1-29 Synthesis of Intermediate 1-29

A reaction was performed in the same manner as in Synthesis Example 1-9except that 40 g of Intermediate 1-2 were used instead of4-iodobromobenzene. As a result, 25.4 g of a white powder were obtained.The powder was identified as Intermediate 1-29 by FD-MS analysis.

Synthesis Example 1-30 Synthesis of Intermediate 1-30

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: acetanilide was used instead of 1-acetamide;and Intermediate 1-29 was used instead of Intermediate 1-6. As a result,20.5 g of a white powder were obtained. The powder was identified asIntermediate 1-30 by FD-MS analysis.

Synthesis Example 1-31 Synthesis of Intermediate 1-31

A reaction was performed in the same manner as in Synthesis Examples 1-4and 1-5 except that: Intermediate 1-11 was used instead of Intermediate1-3; and Intermediate 1-2 was used instead of 4-iodobromobenzene. As aresult, 26 g of a white powder were obtained. The powder was identifiedas Intermediate 1-31 by FD-MS analysis.

Synthesis Example 1-32 Synthesis of Intermediate 1-32

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: acetanilide was used instead of 1-acetamide;and Intermediate 1-31 was used instead of Intermediate 1-6. As a result,19.5 g of a white powder were obtained. The powder was identified asIntermediate 1-32 by FD-MS analysis.

Synthesis Example 1-33 Synthesis of Intermediate 1-33

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: acetanilide was used instead of 1-acetamide;and Intermediate 1-8 was used instead of Intermediate 1-6. As a result,19.8 g of a white powder were obtained. The powder was identified asIntermediate 1-33 by FD-MS analysis.

Synthesis Example 1-34 Synthesis of Intermediate 1-34

A reaction was performed in the same manner as in Synthesis Examples 1-4and 1-5 except that Intermediate 1-2 was used instead of4-iodobromobenzene. As a result, 30 g of a white powder were obtained.The powder was identified as Intermediate 1-34 by FD-MS analysis.

Synthesis Example 1-35 Synthesis of Intermediate 1-35

A reaction was performed in the same manner as in Synthesis Examples1-15 and 1-16 except that: acetanilide was used instead of 1-acetamide;and Intermediate 1-34 was used instead of Intermediate 1-6. As a result,23.2 g of a white powder were obtained. The powder was identified asIntermediate 1-35 by FD-MS analysis.

Synthesis Example 1-36 Synthesis of Intermediate 1-36

Under an argon atmosphere, 600 mL of dry tetrahydrofuran were added to78.0 g of dibenzofuran, and then the mixture was cooled to −30° C. 300milliliters of a solution of n-butyllithium in hexane (1.65 M) weredropped to the mixture, and then the temperature of the whole wasincreased to room temperature over 1 hour while the whole was stirred.After having been stirred at room temperature for 5 hours, the resultantwas cooled to −60° C., and then 60 mL of 1,2-dibromoethane were droppedto the resultant over 1 hour.

After having been stirred at room temperature for 15 hours, the mixturewas poured into 1,000 mL of ice water, and then the organic layer wasextracted with dichloromethane. The organic layer was washed with asaturated salt solution, and was then dried with anhydrous magnesiumsulfate. The dried product was separated by filtration, and was thenconcentrated. The resultant solid was purified by silica gelchromatography (toluene), washed with tetrahydrofuran and methanol, anddried under reduced pressure. As a result, 70 g of a solid wereobtained. The solid was identified as Intermediate 1-36 by FD-MSanalysis.

Synthesis Example 1-37 Synthesis of Intermediate 1-37

Under an argon atmosphere, 1,000 mL of toluene and 500 mL of an aqueoussolution of sodium carbonate having a concentration of 2 M were added to120.0 g (399 mmol) of 1-bromo-3-fluoro-4-iodobenzene, 72.7 g (479 mmol)of 2-methoxyphenyl boronic acid, and 9.2 g (7.96 mmol) oftetrakis(triphenylphosphine)palladium(0), and then the mixture washeated while being refluxed for 10 hours.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 89.6 g of a whitecrystal of 4-bromo-2-fluoro-2′-methoxybiphenyl were obtained (in 80%yield).

Under an argon atmosphere, 900 mL of dichloromethane were added to 89.6g (319 mmol) of 4-bromo-2-fluoro-2′-methoxybiphenyl, and then themixture was stirred under ice cooling. 95.9 grams (382 mmol) of borontribromide were added dropwise to the mixture, and then the whole wasstirred at room temperature for 12 hours. After the completion of thereaction, 200 mL of water were added to the resultant, and then themixture was stirred for 1 hour. After that, the aqueous layer wasremoved. The organic layer was dried with magnesium sulfate, and wasthen concentrated. The residue was purified by silica gel columnchromatography. Thus, 68.1 g of a white crystal of4-bromo-2-fluoro-2′-hydroxybiphenyl were obtained (in 70% yield).

1,500 milliliters of N-methylpyrrolidone were added to 68.1 g (255 mmol)of 4-bromo-2-fluoro-2′-hydroxybiphenyl and 70.4 g (510 mmol) ofpotassium carbonate, and then the mixture was stirred at 180° C. for 3hours. After the completion of the reaction, water was added to theresultant, and then extraction with toluene was performed. The organiclayer was dried with sodium sulfate, and was then concentrated. Theresidue was recrystallized from toluene so as to be purified. Thus, 44.2g of a white crystal of 3-bromodibenzofuran were obtained (in 60%yield). The crystal was identified as Intermediate 1-37 by FD-MSanalysis.

Synthesis Embodiment 1-1 Synthesis of Compound 1-H1

In a stream of argon, 5.0 g of Intermediate 1-20, 3.2 g of Intermediate1-9, 1.3 g of t-butoxy sodium (manufactured by Hiroshima Wako Ltd.), 46mg of tris(dibenzylideneacetone)dipalladium(0) (manufactured by SigmaAldrich Co.), 21 mg of tri-t-butylphosphine, and 50 mL of dry toluenewere loaded and subjected to a reaction at 80° C. for 8 hours.

After the resultant had been cooled, 500 mL of water were added to theresultant, and then the mixture was filtrated with celite. The filtratewas extracted with toluene, and was then dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure. Theresultant coarse product was subjected to column purification, and wasthen recrystallized with toluene. The crystal was taken by filtration,and was then dried. As a result, 4.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H1 (ExemplifiedCompound AD-2 shown above) by FD-MS analysis.

Synthesis Embodiment 1-2 Synthesis of Compound 1-H2

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 4.0 g of Intermediate 1-10 were used instead ofIntermediate 1-9. As a result, 5.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H2 (ExemplifiedCompound AD-14 shown above) by FD-MS analysis.

Synthesis Embodiment 1-3 Synthesis of Compound 1-H3

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 4.9 g of Intermediate 1-21 were used instead ofIntermediate 1-20. As a result, 4.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H3 (ExemplifiedCompound AD-4 shown above) by FD-MS analysis.

Synthesis Embodiment 1-4 Synthesis of Compound 1-H4

A reaction was performed in the same manner as in Synthesis Embodiment1-2 except that 4.9 g of Intermediate 1-21 were used instead ofIntermediate 1-20. As a result, 4.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H4 (ExemplifiedCompound AD-16 shown above) by FD-MS analysis.

Synthesis Embodiment 1-5 Synthesis of Compound 1-H5

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 5.0 g of Intermediate 1-22 were used instead ofIntermediate 1-20. As a result, 5.2 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H5 (ExemplifiedCompound AD-34 shown above) by FD-MS analysis.

Synthesis Embodiment 1-6 Synthesis of Compound 1-H6

A reaction was performed in the same manner as in Synthesis Embodiment1-2 except that 5.0 g of Intermediate 1-22 were used instead ofIntermediate 1-20. As a result, 5.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H6 (ExemplifiedCompound AD-46 shown above) by FD-MS analysis.

A synthesis method has been changed in association with the change ofthe compound in the example (Intermediate 22→28)

Synthesis Embodiment 1-7 Synthesis of Compound 1-H7

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-28 were used instead ofIntermediate 1-20; and 4.0 g of Intermediate 1-12 were used instead ofIntermediate 1-9. As a result, 5.2 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H7 by FD-MS analysis.

Synthesis Embodiment 1-8 Synthesis of Compound 1-H8

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.3 g of Intermediate 1-16 were used instead ofIntermediate 1-20; and 6.4 g of Intermediate 1-9 were used. As a result,2.2 g of a pale yellow powder were obtained. The powder was identifiedas Compound 1-H8 (Exemplified Compound AD-190 shown above) by FD-MSanalysis.

Synthesis Embodiment 1-9 Synthesis of Compound 1-H9

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.7 g of Intermediate 1-17 were used instead ofIntermediate 1-20; and 6.4 g of Intermediate 1-9 were used. As a result,2.3 g of a pale yellow powder were obtained. The powder was identifiedas Compound 1-H9 (Exemplified Compound AD-192 shown above) by FD-MSanalysis.

Synthesis Embodiment 1-10 Synthesis of Compound 1-H10

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.9 g of Intermediate 1-18 were used instead ofIntermediate 1-20; and 6.4 g of Intermediate 1-9 were used. As a result,2.4 g of a pale yellow powder were obtained. The powder was identifiedas Compound 1-H10 (Exemplified Compound AD-194 shown above) by FD-MSanalysis.

Synthesis Embodiment 1-11 Synthesis of Compound 1-H11

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.3 g of Intermediate 1-19 were used instead ofIntermediate 1-20; and 6.4 g of Intermediate 1-9 were used. As a result,1.9 g of a pale yellow powder were obtained. The powder was identifiedas Compound 1-H11 (Exemplified Compound AD-196 shown above) by FD-MSanalysis.

Synthesis Embodiment 1-12 Synthesis of Compound 1-H12

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 3.7 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 4.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H12 (ExemplifiedCompound AD-1 shown above) by FD-MS analysis.

Synthesis Embodiment 1-13 Synthesis of Compound 1-H13

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-22 were used instead ofIntermediate 1-20; and 3.7 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H13 (ExemplifiedCompound AD-33 shown above) by FD-MS analysis.

Synthesis Embodiment 1-14 Synthesis of Compound 1-H14

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-27 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-3 were used instead ofIntermediate 1-9. As a result, 3.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H14 (ExemplifiedCompound AD-191 shown above) by FD-MS analysis.

Synthesis Embodiment 1-15 Synthesis of Compound 1-H15

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.3 g of Intermediate 1-16 were used instead ofIntermediate 1-20; and 7.4 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 2.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H15 (ExemplifiedCompound AD-193 shown above) by FD-MS analysis.

Synthesis Embodiment 1-16 Synthesis of Compound 1-H16

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.3 g of Intermediate 1-19 were used instead ofIntermediate 1-20; and 7.4 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 2.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H16 (ExemplifiedCompound AD-24 shown above) by FD-MS analysis.

Synthesis Embodiment 1-17 Synthesis of Compound 1-H17

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-23 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-3 were used instead ofIntermediate 1-9. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H17 (ExemplifiedCompound AD-195 shown above) by FD-MS analysis.

Synthesis Embodiment 1-18 Synthesis of Compound 1-H18

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-23 were used instead ofIntermediate 1-20; and 4.0 g of Intermediate 1-13 were used instead ofIntermediate 1-9. As a result, 5.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H18 (ExemplifiedCompound AD-120 shown above) by FD-MS analysis.

Synthesis Embodiment 1-19 Synthesis of Compound 1-H19

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-23 were used instead ofIntermediate 1-20; and 3.2 g of Intermediate 1-14 were used instead ofIntermediate 1-9. As a result, 4.9 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H19 (ExemplifiedCompound AD-197 shown above) by FD-MS analysis.

Synthesis Embodiment 1-20 Synthesis of Compound 1-H20

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 3.3 g of Intermediate 1-26 were used instead ofIntermediate 1-20. As a result, 3.9 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H20 (ExemplifiedCompound AD-129 shown above) by FD-MS analysis.

Synthesis Embodiment 1-21 Synthesis of Compound 1-H21

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 1.3 g of Intermediate 1-16 were used instead ofIntermediate 1-20; and 13.2 g of Intermediate 1-24 were used instead ofIntermediate 1-9. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H21 (ExemplifiedCompound AD-151 shown above) by FD-MS analysis.

Synthesis Embodiment 1-22 Synthesis of Compound 1-H22

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 3.3 g of Intermediate 1-26 were used instead ofIntermediate 1-20; and 9.8 g of Intermediate 1-25 were used instead ofIntermediate 1-9. As a result, 5.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H22 (ExemplifiedCompound AD-171 shown above) by FD-MS analysis.

Synthesis Embodiment 1-23 Synthesis of Compound 1-H23

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.0 g of Intermediate 1-23 were used instead ofIntermediate 1-20; and 9.8 g of tris(4-bromophenyl)amine were usedinstead of Intermediate 1-9. As a result, 3.8 g of a pale yellow powderwere obtained. The powder was identified as Compound 1-H23 (ExemplifiedCompound AD-187 shown above) by FD-MS analysis.

Synthesis Embodiment 1-24 Synthesis of Compound 1-H24

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that 4.0 g of Intermediate 1-12 were used instead ofIntermediate 1-9. As a result, 5.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H24 by FD-MS analysis.

Synthesis Embodiment 1-25 Synthesis of Compound 1-H25

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 4.5 g of Intermediate 1-30 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-36 were used instead ofIntermediate 1-9. As a result, 3.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H25 by FD-MS analysis.

Synthesis Embodiment 1-26 Synthesis of Compound 1-H26

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 4.5 g of Intermediate 1-30 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-3 were used instead ofIntermediate 1-9. As a result, 3.5 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H26 by FD-MS analysis.

Synthesis Embodiment 1-27 Synthesis of Compound 1-H27

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 4.5 g of Intermediate 1-30 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-37 were used instead ofIntermediate 1-9. As a result, 3.9 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H27 by FD-MS analysis.

Synthesis Embodiment 1-28 Synthesis of Compound 1-H28

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.3 g of Intermediate 1-32 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-37 were used instead ofIntermediate 1-9. As a result, 4.0 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H28 by FD-MS analysis.

Synthesis Embodiment 1-29 Synthesis of Compound 1-H29

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.3 g of Intermediate 1-32 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-3 were used instead ofIntermediate 1-9. As a result, 3.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H29 by FD-MS analysis.

Synthesis Embodiment 1-30 Synthesis of Compound 1-H30

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 5.3 g of Intermediate 1-32 were used instead ofIntermediate 1-20; and 2.5 g of Intermediate 1-37 were used instead ofIntermediate 1-9. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H30 by FD-MS analysis.

Synthesis Embodiment 1-31 Synthesis of Compound 1-H31

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 4.5 g of Intermediate 1-33 were used instead ofIntermediate 1-20; and 3.7 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 4.2 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H31 by FD-MS analysis.

Synthesis Embodiment 1-32 Synthesis of Compound 1-H32

A reaction was performed in the same manner as in Synthesis Embodiment1-1 except that: 4.5 g of Intermediate 1-35 were used instead ofIntermediate 1-20; and 3.7 g of Intermediate 1-11 were used instead ofIntermediate 1-9. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 1-H32 by FD-MS analysis.

The structural formulae of Intermediates 1-1 to 1-37 synthesized inSynthesis Examples 1-1 to 1-37 described above, Compounds 1-H1 to 1-H32synthesized in Synthesis Embodiments 1-1 to 1-32 each serving as thearomatic amine derivative of the present invention, and ComparativeCompounds 1-1 to 1-6 are as shown below.

Example 1-1 Production of Organic EL Device

A glass substrate with an ITO transparent electrode measuring 25 mm wideby 75 mm long by 1.1 mm thick (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.After that, the substrate was subjected to UV ozone cleaning for 30minutes.

The glass substrate with the transparent electrode line after thecleaning was mounted on a substrate holder of a vacuum vapor depositiondevice. First, the following compound H232 was deposited from vapor onthe surface on the side where the transparent electrode line was formedso as to cover the transparent electrode. Then, the H232 film having athickness of 60 nm was formed as the hole injecting layer. Theabove-mentioned compound 1-H1 was deposited from vapor and formed into ahole transporting layer having a thickness of 20 nm on the H232 film.Further, the following compound EM1 was deposited from vapor and formedinto a light emitting layer having a thickness of 40 nm. Simultaneouslywith this formation, the following amine compound D1 having a styrylgroup, as a light emitting molecule, was deposited from vapor in such amanner that a weight ratio between the compound EM1 and the aminecompound D1 was 40:2.

The following Alq was formed into a film having a thickness of 10 nm onthe resultant film. The film functions as an electron injecting layer.After that, Li serving as a reducing dopant (Li source: manufactured bySAES Getters) and Alq were subjected to co-vapor deposition. Thus, anAlq:Li film (having a thickness of 10 nm) was formed as an electroninjecting layer (cathode). Metal Al was deposited from vapor onto theAlq:Li film to form a metal cathode. Thus, an organic EL device wasformed.

Next, after the resultant organic EL device had been stored at 105° C.for 8 hours, the luminous efficiency of the organic EL device wasmeasured, and the luminescent color of the device was observed. Aluminous efficiency at 10 mA/cm² was calculated by measuring a luminanceby using a CS1000 manufactured by Minolta. Further, the half lifetime ofemitted light in DC constant current driving at an initial luminance of5,000 cd/m² and room temperature was measured. Table 1 shows theresults.

Examples 1-2 to 1-11 Production of Organic EL Device

Each organic EL device was produced in the same manner as in Example 1-1except that the respective compounds shown in Table 1 were used as holetransporting materials instead of the compound 1-H1.

The luminous efficiency of the resultant organic EL device was measured,and the luminescent color of the device was observed in the same manneras in Example 1-1. Further, the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 1 shows the results.

Comparative Examples 1-1 to 1-6

Each organic EL device was produced in the same manner as in Example 1-1except that the respective comparative compounds 1-1 to 1-6 were used ashole transporting materials instead of the compound 1-H1.

Further, in the same manner as in Example 1-1, the luminous efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 1 shows the results.

Example 1-12 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 1-1except that the following arylamine compound 1D2 was used instead of theamine compound D1 having a styryl group. Me represents a methyl group.

Further, in the same manner as in Example 1-1, the luminous efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 1 shows the results.

Comparative Example 1-7

An organic EL device was produced in the same manner as in Example 1-12except that the above-mentioned comparative compound 1-4 was used as ahole transporting material instead of the compound 1-H1.

Further, in the same manner as in Example 1-1, the luminous efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 1 shows the results.

TABLE 1 Hole Luminous Half transporting efficiency Luminescent lifetimeExample material (cd/A) color (h) 1-1 1-H1 6.2 Blue 380 1-2 1-H2 6.0Blue 420 1-3 1-H3 6.1 Blue 390 1-4 1-H4 5.9 Blue 430 1-5 1-H5 6.4 Blue360 1-6 1-H6 6.3 Blue 410 1-7 1-H7 5.7 Blue 430 1-8 1-H19 5.6 Blue 3301-9 1-H25 6.4 Blue 370 1-10 1-H26 6.4 Blue 370 1-11 1-H27 6.4 Blue 3701-12 1-H1 6.1 Blue 390 Comparative Comparative 3.1 Blue 100 Example 1-1Compound 1-1 Comparative Comparative 1.5 Blue 120 Example 1-2 Compound1-2 Comparative Comparative 1.2 Blue 60 Example 1-3 Compound 1-3Comparative Comparative 3.9 Blue 160 Example 1-4 Compound 1-4Comparative Comparative 5.2 Blue 150 Example 1-5 Compound 1-5Comparative Comparative 4.9 Blue 230 Example 1-6 Compound 1-6Comparative Comparative 4.1 Blue 130 Example 1-7 Compound 1-4

As is apparent from the results of Table 1, an organic EL device usingthe aromatic amine derivative of the present invention provides highluminous efficiency even at high temperatures and has a long halflifetime as compared with an organic EL device using an aromatic aminederivative for comparison.

Synthesis Example 2-1 Synthesis of Intermediate 2-1

Under an argon stream, to a 1,000-mL three-necked flask, 47 g of4-bromobiphenyl, 23 g of iodine, 9.4 g of periodic acid dihydrate, 42 mLof water, 360 mL of acetic acid, and 11 mL of sulfuric acid werecharged, and the mixture was stirred at 65° C. for 30 minutes and wasthen subjected to a reaction at 90° C. for 6 hours. The reactant waspoured into ice water, followed by filtering. The resultant was washedwith water, and then washed with methanol, whereby 67 g of a whitepowder were obtained. Main peaks having ratios m/z of 358 and 360 withrespect to C₁₂H₈BrI=359 were obtained by a field desorption massspectrometry (hereinafter, FD-MS) analysis, so the white powder wasidentified as Intermediate 2-1.

Synthesis Example 2-2 Synthesis of Intermediate 2-2

A reaction was performed in the same manner as in Synthesis Example 2-1except that 2-bromo-9,9-dimethylfluorene was used instead of4-bromobiphenyl. As a result, 61 g of a white powder were obtained. Thepowder was identified as Intermediate 2-2 by FD-MS analysis because mainpeaks having ratios m/z of 398 and 400 were obtained with respect toC₁₅H₁₂BrI=399.

Synthesis Example 2-3 Synthesis of Intermediate 2-3

150 grams (892 mmol) of dibenzofuran and 1 L of acetic acid were loadedinto a flask. The air in the flask was replaced with nitrogen, and thenthe contents were dissolved under heat. 188 grams (1.18 mol) of brominewere dropped to the solution while the flask was sometimes cooled withwater. After that, the mixture was stirred for 20 hours under aircooling. The precipitated crystal was separated by filtration, and wasthen sequentially washed with acetic acid and water. The washed crystalwas dried under reduced pressure. The resultant crystal was purified bydistillation under reduced pressure, and was then repeatedlyrecrystallized with methanol several times. Thus, 66.8 g of2-bromodibenzofuran were obtained (in 31% yield). The resultant wasidentified as Intermediate 2-3 by FD-MS analysis.

Synthesis Example 2-4 Synthesis of Intermediate 2-4

Under an argon atmosphere, 400 mL of anhydrous THF were added to 24.7 g(100 mmol) of 2-bromodibenzofuran, and then 63 mL (100 mmol) of asolution of n-butyllithium in hexane having a concentration of 1.6 Mwere added to the mixture during the stirring of the mixture at −40° C.The reaction solution was stirred for 1 hour while being heated to 0° C.The reaction solution was cooled to −78° C. again, and then a solutionof 26.0 g (250 mmol) of trimethyl borate in 50 mL of dry THF was droppedto the solution. The reaction solution was stirred at room temperaturefor 5 hours. 200 milliliters of 1N hydrochloric acid were added to thesolution, and then the mixture was stirred for 1 hour. After that, theaqueous layer was removed. The organic layer was dried with magnesiumsulfate, and then the solvent was removed by distillation under reducedpressure. The resultant solid was washed with toluene. Thus, 15.2 g ofdibenzofuran-2-boronic acid were obtained (in 72% yield). The resultantwas identified as Intermediate 2-4 by FD-MS analysis because a main peakhaving a ratio m/z of 212 was obtained with respect to C₁₂H₉BO₃=212.

Synthesis Example 2-5 Synthesis of Intermediate 2-5

Under an argon atmosphere, 300 mL of toluene and 150 mL of an aqueoussolution of sodium carbonate having a concentration of 2 M were added to28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) ofdibenzofuran-2-boronic acid (Intermediate 2-4), and 2.31 g (2.00 mmol)of tetrakis(triphenylphosphine) palladium(0), and then the mixture washeated while being refluxed for 10 hours.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 26.2 g of a whitecrystal of 4-(4-bromophenyl)dibenzofuran were obtained (in 81% yield).The crystal was identified as Intermediate 2-5 by FD-MS analysis.

Synthesis Example 2-6 Synthesis of Intermediate 2-6

A reaction was performed in the same manner as in Synthesis Example 2-5except that 35.9 g of Intermediate 2-1 were used instead of4-iodobromobenzene. As a result, 28.1 g, of a white powder wereobtained. The powder was identified as Intermediate 2-6 by FD-MSanalysis.

Synthesis Example 2-7 Synthesis of Intermediate 2-7

A reaction was performed in the same manner as in Synthesis Example 2-5except that 39.9 g of Intermediate 2-2 were used instead of4-iodobromobenzene. As a result, 27.5 g of a white powder were obtained.The powder was identified as Intermediate 2-7 by FD-MS analysis.

Synthesis Example 2-8 Synthesis of Intermediate 2-8

A reaction was performed in the same manner as in Synthesis Example 2-5except that 22.3 g of dibenzofuran-4-boronic acid were used instead ofdibenzofuran-2-boronic acid. As a result, 23.1 g of a white powder wereobtained. The powder was identified as Intermediate 2-8 by FD-MSanalysis.

Synthesis Example 2-9 Synthesis of Intermediate 2-9

A reaction was performed in the same manner as in Synthesis Example 2-8except that 36 g of Intermediate 2-1 were used instead of4-iodobromobenzene. As a result, 28.1 g of a white powder were obtained.The powder was identified as Intermediate 2-9 by FD-MS analysis.

Synthesis Example 2-10 Synthesis of Intermediate 2-10

A reaction was performed in the same manner as in Synthesis Example 2-8except that 40 g of Intermediate 2-2 were used instead of4-iodobromobenzene. As a result, 30.2 g of a white powder were obtained.The powder was identified as Intermediate 2-10 by FD-MS analysis.

Synthesis Example 2-11 Synthesis of Intermediate 2-11

In a stream of argon, 16.8 g of diphenylamine, 36.0 g of Intermediate2-1, 10 g of t-butoxy sodium (manufactured by Hiroshima Wako Ltd.), 1.6g of bis(triphenylphosphine)palladium(II) chloride (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded andsubjected to a reaction at 130° C. for 24 hours.

After the resultant had been cooled, 1,000 mL of water were added to theresultant, and then the mixture was filtrated with celite. The filtratewas extracted with toluene, and was then dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure. Theresultant coarse product was subjected to column purification, and wasthen recrystallized with toluene. The crystal was taken by filtration,and was then dried. As a result, 12.4 g of a pale yellow powder wereobtained. The powder was identified as Intermediate 2-11 by FD-MSanalysis.

Synthesis Example 2-12 Synthesis of Intermediate 2-12

A reaction was performed in the same manner as in Synthesis Example 2-11except that 4-iodobromobenzene was used instead of Intermediate 2-1. Asa result, 9.3 g of a white powder were obtained. The powder wasidentified as Intermediate 2-12 by FD-MS analysis.

Synthesis Example 2-13 Synthesis of Intermediate 2-13

In a stream of argon, 185 g of 1-acetamide (manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), 323 g of Intermediate 2-8 (manufactured byWako Pure Chemical Industries, Ltd.), 544 g of potassium carbonate(manufactured by Wako Pure Chemical Industries, Ltd.), 12.5 g of acopper powder (manufactured by Wako Pure Chemical Industries, Ltd.), and2 L of decalin were loaded and subjected to a reaction at 190° C. for 4days. After the reaction, the resultant was cooled, and then 2 L oftoluene were added to the resultant. The insoluble portion was taken byfiltration. The product taken by filtration was dissolved in 4.5 L ofchloroform, and then the insoluble portion was removed. After that, theremainder was subjected to an activated carbon treatment andconcentrated. 3 liters of acetone were added to the resultant, and then181 g of the precipitated crystal were taken by filtration. The crystalwas identified as Intermediate 2-13 by FD-MS analysis.

Synthesis Example 2-14 Synthesis of Intermediate 2-14

A reaction was performed in the same manner as in Synthesis Example 2-13except that the usage of Intermediate 2-8 was changed from 323 g to 678g. As a result, 330 g of a white powder were obtained. Further, in astream of argon, the resultant white powder was suspended in 5 L ofethylene glycol (manufactured by Wako Pure Chemical Industries, Ltd.)and 50 mL of water, and then 210 g of an 85% aqueous solution ofpotassium hydroxide were added to the suspension. After that, themixture was subjected to a reaction at 120° C. for 8 hours. After thereaction, the reaction liquid was injected into 10 L of water, and thenthe precipitated crystal was taken by filtration. The crystal was washedwith water and methanol. The resultant crystal was dissolved in 3 L oftetrahydrofuran under heat. The solution was subjected to an activatedcarbon treatment, and was then concentrated. Acetone was added to theresultant to precipitate a crystal. The crystal was taken by filtration.Thus, 198 g of a white powder were obtained. The powder was identifiedas Intermediate 2-14 by FD-MS analysis.

Synthesis Example 2-15 Synthesis of Intermediate 2-15

A reaction was performed in the same manner as in Synthesis Example 2-14except that Intermediate 2-5 was used instead of Intermediate 2-8. As aresult, 221 g of a white powder were obtained. The powder was identifiedas Intermediate 2-15 by FD-MS analysis.

Synthesis Example 2-16 Synthesis of Intermediate 2-16

A reaction was performed in the same manner as in Synthesis Example 2-13except that: Intermediate 2-13 was used instead of 1-acetamide; andIntermediate 2-5 was used instead of Intermediate 2-8. As a result, 190g of a white powder were obtained. The powder was identified asIntermediate 2-16 by FD-MS analysis.

Synthesis Example 2-17 Synthesis of Intermediate 2-17

A reaction was performed in the same manner as in Synthesis Example 2-11except that: Intermediate 2-16 was used instead of diphenylamine; and4-iodobromobenzene was used instead of Intermediate 2-1. As a result, 45g of a white powder were obtained. The powder was identified asIntermediate 2-17 by FD-MS analysis.

Synthesis Example 2-18 Synthesis of Intermediate 2-18

A reaction was performed in the same manner as in Synthesis Example 2-11except that Intermediate 2-16 was used instead of diphenylamine. As aresult, 56 g of a white powder were obtained. The powder was identifiedas Intermediate 2-18 by FD-MS analysis.

Synthesis Example 2-19 Synthesis of Intermediate 2-19

Under an argon atmosphere, 600 mL of dry tetrahydrofuran were added to78.0 g of dibenzofuran, and then the mixture was cooled to −30° C. 300milliliters of a solution of n-butyllithium in hexane (1.65 M) weredropped to the mixture, and then the temperature of the whole wasincreased to room temperature over 1 hour while the whole was stirred.After having been stirred at room temperature for 5 hours, the resultantwas cooled to −60° C., and then 60 mL of 1,2-dibromoethane were droppedto the resultant over 1 hour.

After having been stirred at room temperature for 15 hours, the mixturewas poured into 1,000 mL of ice water, and then the organic layer wasextracted with dichloromethane. The organic layer was washed with asaturated salt solution, and was then dried with anhydrous magnesiumsulfate. The dried product was separated by filtration, and was thenconcentrated. The resultant solid was purified by silica gelchromatography (toluene), washed with tetrahydrofuran and methanol, anddried under reduced pressure. As a result, 70 g of a solid wereobtained. The solid was identified as Intermediate 2-19 by FD-MSanalysis.

Synthesis Example 2-20 Synthesis of Intermediate 2-20

Under an argon atmosphere, 1,000 mL of toluene and 500 mL of an aqueoussolution of sodium carbonate having a concentration of 2M were added to120.0 g (399 mmol) of 1-bromo-3-fluoro-4-iodobenzene, 72.7 g (479 mmol)of 2-methoxyphenyl boronic acid, and 9.2 g (7.96 mmol) oftetrakis(triphenylphosphine)palladium(0), and then the mixture washeated while being refluxed for 10 hours.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 89.6 g of a whitecrystal of 4-bromo-2-fluoro-2′-methoxybiphenyl were obtained (in 80%yield).

Under an argon atmosphere, 900 mL of dichloromethane were added to 89.6g (319 mmol) of 4-bromo-2-fluoro-2′-methoxybiphenyl, and then themixture was stirred under ice cooling. 95.9 g (382 mmol) of borontribromide were added dropwise to the mixture, and then the whole wasstirred at room temperature for 12 hours. After the completion of thereaction, 200 mL of water were added to the resultant, and then themixture was stirred for 1 hour. After that, the aqueous layer wasremoved. The organic layer was dried with magnesium sulfate, and wasthen concentrated. The residue was purified by silica gel columnchromatography. Thus, 68.1 g of a white crystal of4-bromo-2-fluoro-2′-hydroxybiphenyl were obtained (in 70% yield).

1,500 milliliters of N-methylpyrrolidone were added to 68.1 g (255 mmol)of 4-bromo-2-fluoro-2′-hydroxybiphenyl and 70.4 g (510 mmol) ofpotassium carbonate, and then the mixture was stirred at 180° C. for 3hours. After the completion of the reaction, water was added to theresultant, and then extract ion with toluene was performed. The organiclayer was dried with sodium sulfate, and was then concentrated. Theresidue was recrystallized from toluene so as to be purified. Thus, 44.2g of a white crystal were obtained (in 60% yield). The crystal wasidentified as Intermediate 2-20 by FD-MS analysis.

Synthesis Example 2-21 Synthesis of Intermediate 2-21

Under an argon atmosphere, 350 mL of toluene and 170 mL of an aqueoussolution of sodium carbonate having a concentration of 2 M were added to34.2 g (138 mmol) of Intermediate 2-20, 26.0 g (166 mmol) of4-chlorophenyl boronic acid, and 3.2 g (2.77 mmol) oftetrakis(triphenylphosphine)palladium(0), and then the mixture washeated while being refluxed for 12 hours.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 23.1 g of a whitecrystal were obtained (in 60% yield). The crystal was identified asIntermediate 2-21 by FD-MS analysis.

Synthesis Example 2-22 Synthesis of Intermediate 2-22

A reaction was performed in the same manner as in Synthesis Example 2-14except that Intermediate 2-21 was used instead of Intermediate 2-8. As aresult, 35 g of a white powder were obtained. The powder was identifiedas Intermediate 2-22 by FD-MS analysis.

Synthesis Embodiment 2-1 Synthesis of Compound 2-H1

In a stream of argon, 5.0 g of Intermediate 2-14, 3.2 g of Intermediate2-5, 1.3 g of t-butoxy sodium (manufactured by Hiroshima Wako Ltd.), 46mg of tris(dibenzylideneacetone)dipalladium(0) (manufactured by SigmaAldrich Co.), 21 mg of tri-t-butylphosphine, and 50 mL of dry toluenewere loaded and subjected to a reaction at 80° C. for 8 hours.

After the resultant had been cooled, 500 mL of water were added to theresultant, and then the mixture was filtrated with celite. The filtratewas extracted with toluene, and was then dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure. Theresultant coarse product was subjected to column purification, and wasthen recrystallized with toluene. The crystal was taken by filtration,and was then dried. As a result, 4.3 g of a pale yellow powder wereobtained. The powder was identified as Intermediate 2-H1 by FD-MSanalysis.

Synthesis Embodiment 2-2 Synthesis of Compound 2-H2

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that 4.0 g of Intermediate 2-6 were used instead ofIntermediate 2-5. As a result, 5.3 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H2 by FD-MS analysis.

Synthesis Embodiment 2-3 Synthesis of Compound 2-H3

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that 4.9 g of Intermediate 2-7 were used instead ofIntermediate 2-5. As a result, 4.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H3 by FD-MS analysis.

Synthesis Embodiment 2-4 Synthesis of Compound 2-H4

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-15 were used instead ofIntermediate 2-14; and 3.2 g of Intermediate 2-8 were used instead ofIntermediate 2-5. As a result, 3.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H4 by FD-MS analysis.

Synthesis Embodiment 2-5 Synthesis of Compound 2-H5 Synthesis Embodiment2-5 Synthesis of Compound 2-H5

A reaction was performed in the same manner as in Synthesis Embodiment2-4 except that 4.0 g of Intermediate 2-9 were used instead ofIntermediate 2-8. As a result, 4.2 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H5 by FD-MS analysis.

Synthesis Embodiment 2-6 Synthesis of Compound 2-H6

A reaction was performed in the same manner as in Synthesis Embodiment2-4 except that 4.4 g of Intermediate 2-10 were used instead ofIntermediate 2-8. As a result, 5.1 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H6 by FD-MS analysis.

Synthesis Embodiment 2-7 Synthesis of Compound 2-H7

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that 4.0 g of Intermediate 2-9 were used instead ofIntermediate 2-5. As a result, 4.5 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H7 by FD-MS analysis.

Synthesis Embodiment 2-8 Synthesis of Compound 2-H8

A reaction was performed in the same manner as in Synthesis Embodiment2-4 except that 4.0 g of Intermediate 2-6 were used instead ofIntermediate 2-8. As a result, 4.2 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H8 by FD-MS analysis.

Synthesis Embodiment 2-9 Synthesis of Compound 2-H9

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-16 were used instead ofIntermediate 2-14; and 3.2 g of Intermediate 2-12 were used instead ofIntermediate 2-5. As a result, 3.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H9 by FD-MS analysis.

Synthesis Embodiment 2-10 Synthesis of Compound 2-H10

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 1.9 g of Intermediate 2-16 were used instead ofIntermediate 2-14; and 4.0 g of Intermediate 2-11 were used instead ofIntermediate 2-5. As a result, 4.5 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H10 by FD-MS analysis.

Synthesis Embodiment 2-11 Synthesis of Compound 2-H11

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-16 were used instead ofIntermediate 2-14; and 1.6 g of 4,4′-dibromobiphenyl were used insteadof Intermediate 2-5. As a result, 2.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H11 by FD-MS analysis.

Synthesis Embodiment 2-12 Synthesis of Compound 2-H12

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 0.4 g of aniline was used instead of Intermediate 2-14;and 7.3 g of Intermediate 2-18 were used instead of Intermediate 2-5. Asa result, 2.1 g of a pale yellow powder were obtained. The powder wasidentified as Compound 2-H12 by FD-MS analysis.

Synthesis Embodiment 2-13 Synthesis of Compound 2-H13

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 0.9 g of N,N′-diphenylbenzidine was used instead ofIntermediate 2-14; and 6.6 g of Intermediate 2-17 were used instead ofIntermediate 2-5. As a result, 2.4 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H13 by FD-MS analysis.

Synthesis Embodiment 2-14 Synthesis of Compound 2-H14

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-16 were used instead ofIntermediate 2-14; and 1.6 g of tris(4-bromophenyl)amine were usedinstead of Intermediate 2-5. As a result, 1.8 g of a pale yellow powderwere obtained. The powder was identified as Compound 2-H14 by FD-MSanalysis.

Synthesis Embodiment 2-15 Synthesis of Compound 2-H15

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-16 were used instead ofIntermediate 2-14; and 3.0 g of 4-bromo-p-terphenyl were used instead ofIntermediate 2-5. As a result, 3.5 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H15 by FD-MS analysis.

Synthesis Embodiment 2-16 Synthesis of Compound 2-H16

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that 2.5 g of Intermediate 2-3 were used instead ofIntermediate 2-5. As a result, 4.1 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H16 by FD-MS analysis.

Synthesis Embodiment 2-17 Synthesis of Compound 2-H17

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that 2.5 g of Intermediate 2-20 were used instead ofIntermediate 2-5. As a result, 3.9 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H17 by FD-MS analysis.

Synthesis Embodiment 2-18 Synthesis of Compound 2-H18

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-15 were used instead ofIntermediate 2-14; and 2.5 g of Intermediate 2-19 were used instead ofIntermediate 2-5. As a result, 3.8 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H18 by FD-MS analysis.

Synthesis Embodiment 2-19 Synthesis of Compound 2-H19

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-15 were used instead ofIntermediate 2-14; and 2.5 g of Intermediate 2-20 were used instead ofIntermediate 2-5. As a result, 3.6 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H19 by FD-MS analysis.

Synthesis Embodiment 2-20 Synthesis of Compound 2-H20

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-22 were used instead ofIntermediate 2-14; and 2.5 g of Intermediate 2-19 were used instead ofIntermediate 2-5. As a result, 4.0 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H20 by FD-MS analysis.

Synthesis Embodiment 2-21 Synthesis of Compound 2-H21

A reaction was performed in the same manner as in Synthesis Embodiment2-1 except that: 5.0 g of Intermediate 2-22 were used instead ofIntermediate 2-14; and 2.5 g of Intermediate 2-3 were used instead ofIntermediate 2-5. As a result, 4.1 g of a pale yellow powder wereobtained. The powder was identified as Compound 2-H21 by FD-MS analysis.

The structural formulae of Intermediates 2-1 to 2-22 synthesized inSynthesis Examples 2-1 to 2-22 described above, Compounds 2-H1 to 2-H21synthesized in Synthesis Embodiments 2-1 to 2-21 each serving as thearomatic amine derivative of the present invention, and ComparativeCompounds 2-1 to 2-7 are as shown below.

Example 2-1 Production of Organic EL Device

A glass substrate with an ITO transparent electrode measuring 25 mm wideby 75 mm long by 1.1 mm thick (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.After that, the substrate was subjected to UV ozone cleaning for 30minutes.

The glass substrate with the transparent electrode line after thecleaning was mounted on a substrate holder of a vacuum vapor depositiondevice. First, the following compound H232 was deposited from vapor onthe surface on the side where the transparent electrode line was formedso as to cover the transparent electrode. Then, the H232 film having athickness of 60 nm was formed as the hole injecting layer. Theabove-mentioned compound 2-H1 was deposited from vapor and formed into ahole transporting layer having a thickness of 20 nm on the H232 film.Further, the following compound EM1 was deposited from vapor and formedinto a light emitting layer having a thickness of 40 nm. Simultaneouslywith this formation, the following amine compound D1 having a styrylgroup, as a light emitting molecule, was deposited from vapor in such amanner that a weight ratio between the compound EM1 and the aminecompound D1 was 40:2.

The following Alq was formed into a film having a thickness of 10 nm onthe resultant film. The film functions as an electron injecting layer.After that, Li serving as a reducing dopant (Li source: manufactured bySAES Getters) and Alq were subjected to co-vapor deposition. Thus, anAlq:Li film (having a thickness of 10 nm) was formed as an electroninjecting layer (cathode). Metal Al was deposited from vapor onto theAlq:Li film to form a metal cathode. Thus, an organic EL device wasformed.

Next, after the resultant organic EL device had been stored at 105° C.for 8 hours, the luminous efficiency of the organic EL device wasmeasured, and the luminescent color of the device was observed. Aluminous efficiency at 10 mA/cm² was calculated by measuring a luminanceby using a CS1000 manufactured by Minolta. Further, the half lifetime ofemitted light in DC constant current driving at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2-1 shows theresults.

Examples 2-2 to 2-8 Production of Organic EL Device

Each organic EL device was produced in the same manner as in Example 2-1except that the respective compounds shown in Table 2 were used as holetransporting materials instead of the compound 2-H1.

In the same manner as in Example 2-1, the luminous efficiency of theresultant organic EL device was measured, the luminescent color of thedevice was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 2 shows the results.

Comparative Examples 2-1 to 2-7

Each organic EL device was produced in the same manner as in Example 2-1except that the respective comparative compounds 2-1 to 2-7 were used ashole transporting materials instead of the compound 2-H1.

Further, in the same manner as in Example 2-1, the luminous efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 2 shows the results.

Example 2-9 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 2-1except that the following arylamine compound D2 was used instead of theamine compound D1 having a styryl group. Me represents a methyl group.

In addition, in the same manner as in Example 2-1, the luminousefficiency of the resultant organic EL device was measured, theluminescent color of the device was observed, and the half lifetime ofemitted light in DC constant current driving at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

Comparative Example 2-8

An organic EL device was produced in the same manner as in Example 2-9except that the above-mentioned comparative compound 2-1 was used as ahole transporting material instead of the compound 2-H1.

Further, in the same manner as in Example 2-1, the luminous efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of emitted light in DCconstant current driving at an initial luminance of 5,000 cd/m² and roomtemperature was measured. Table 2-1 shows the results.

TABLE 2 Hole Luminous Half transporting efficiency Luminescent lifetimeExample material (cd/A) color (h) 2-1 2-H1 6.0 Blue 430 2-2 2-H2 5.9Blue 420 2-3 2-H4 6.3 Blue 390 2-4 2-H5 6.2 Blue 370 2-5 2-H7 6.1 Blue350 2-6 2-H8 6.2 Blue 320 2-7 2-H10 5.8 Blue 310 2-8 2-H15 6.1 Blue 4102-9 2-H1 6.0 Blue 420 Comparative Comparative 3.1 Blue 100 Example 2-1Compound 2-1 Comparative Comparative 1.5 Blue 120 Example 2-2 Compound2-2 Comparative Comparative 1.2 Blue 60 Example 2-3 Compound 2-3Comparative Comparative 4.2 Blue 140 Example 2-4 Compound 2-4Comparative Comparative 4.6 Blue 150 Example 2-5 Compound 2-5Comparative Comparative 5.1 Blue 210 Example 2-6 Compound 2-6Comparative Comparative 5.6 Blue 250 Example 2-7 Compound 2-7Comparative Comparative 3.2 Blue 120 Example 2-8 Compound 2-1

As is apparent from the results of Table 2, an organic EL device usingthe aromatic amine derivative of the present invention provides highluminous efficiency even at high temperatures and has a long halflifetime as compared with an organic EL device using an aromatic aminederivative for comparison.

INDUSTRIAL APPLICABILITY

As described above in detail, the molecules of the aromatic aminederivative of the present invention hardly crystallize, and theincorporation of the derivative into an organic thin film layer improvesa yield upon production of an organic EL device and can realize anorganic EL device having high efficiency and a long lifetime.Accordingly, the derivative is extremely useful as a material for anorganic EL device having high practicality.

The invention claimed is:
 1. An aromatic amine compound represented byany one of the following formulae (5) to (9):

wherein: one of Ar² to Ar⁴ represents a substituent A, one of Ar² to Ar⁴represents a substituent B, and one of Ar² to Ar⁴ represents a groupselected from a substituent A, a substituent B and a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms; one of Ar⁵ toAr⁸ represents a substituent A, one of Ar⁵ to Ar⁸ represents asubstituent B, and the rest of Ar⁵ to Ar⁸ represent a group selectedfrom the group consisting of a substituent A, a substituent B and asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms; one of Ar⁹ to Ar¹³ represents a substituent A, one of Ar⁹ to Ar¹³represents a substituent B, and the rest of Ar⁹ to Ar¹³ represent agroup selected from the group consisting of a substituent A, asubstituent B and a substituted or unsubstituted aryl group having 6 to50 ring carbon atoms; one of Ar¹⁴ to Ar¹⁹ represents a substituent A,one of Ar¹⁴ to Ar¹⁹ represents a substituent B, and the rest of Ar¹⁴ toAr¹⁹ represent a group selected from the group consisting of asubstituent A, a substituent B and a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms; one of Ar²⁰ to Ar²⁵ represents asubstituent A, one of Ar²⁰ to Ar²⁵ represents a substituent B, and therest of Ar²⁰ to Ar²⁵ represent a group selected from the groupconsisting of a substituent A, a substituent B and a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms; thesubstituent A and the substituent B are different from each other; thesubstituent A and the substituent B are each independently representedby formula (1):

wherein: L¹ represents a substituted or unsubstituted divalent arylenegroup having 6 to 50 ring carbon atoms, wherein the optional substituentof L¹ is selected from the group consisting of a linear or branchedalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms,a triarylsilyl group having 18 to 30 ring carbon atoms, analkylarylsilyl group having 8 to 15 carbon atoms whose aryl portion has6 to 14 ring carbon atoms, an aryl group having 6 to 14 ring carbonatoms, a halogen atom, and a cyano group, and wherein a plurality ofsuch substituents adjacent to each other may be bonded to each other toform a saturated or unsaturated ring; a represents an integer of 0 to 4;b represents an integer of 0 to 3; R¹ and R² each independentlyrepresent a linear or branched alkyl group having 1 to 10 carbon atoms,a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilylgroup having 3 to 10 carbon atoms, a triarylsilyl group having 18 to 30ring carbon atoms, an alkylarylsilyl group having 8 to 15 carbon atomswhose aryl portion has 6 to 14 ring carbon atoms, an aryl group having 6to 14 ring carbon atoms, a halogen atom, or a cyano group, and aplurality of R¹'s and R²'s adjacent to each other may be bonded to eachother to form a saturated or unsaturated, divalent group that forms aring, and wherein the optional substituents on the substituted orunsubstituted aryl group are selected from the group consisting of alinear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkylgroup having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3to 10 carbon atoms, a triarylsilyl group having 18 to 30 ring carbonatoms, an alkylarylsilyl group having 8 to 15 carbon atoms whose arylportion has 6 to 14 ring carbon atoms, an aryl group having 6 to 14 ringcarbon atoms, a halogen atom, or a cyano group, and the adjacentoptional substituents may be bonded to each other to form a saturated orunsaturated, divalent group that forms a ring; L⁴ to L¹² eachindependently represent a substituted or unsubstituted divalent arylenegroup having 6 to 50 ring carbon atoms; and the substituents which L⁴ toL¹² may have are each independently selected from the group consistingof a linear or branched alkyl group having 1 to 10 carbon atoms, acycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl grouphaving 3 to 10 carbon atoms, a triarylsilyl group having 18 to 30 ringcarbon atoms, an alkylarylsilyl group having 8 to 15 carbon atoms whosearyl portion has 6 to 14 ring carbon atoms, an aryl group having 6 to 14ring carbon atoms, a halogen atom, and a cyano group, and wherein aplurality of such substituents adjacent to each other may be bonded toeach other to form a saturated or unsaturated ring.
 2. The aromaticamine compound according to claim 1, wherein the substituent A and thesubstituent B are each independently represented by any one of thefollowing formulae (1-1) to (1-3):


3. The aromatic amine compound according to claim 2, wherein thesubstituent A is represented by the formula (1-1) and the substituent Bis represented by the formula (1-2).
 4. The aromatic amine compoundaccording to claim 2, wherein the substituent A is represented by thefollowing formula (1-1) or (1-2):


5. The aromatic amine compound according to claim 2, wherein thearomatic amine compound is represented by the formula (5) in which theAr² to Ar⁴ are each represented by the formula (1-2).
 6. The aromaticamine compound according to claim 2, wherein the aromatic amine compoundis represented by the formula (5) in which the Ar² to Ar⁴ are eachrepresented by the formula (1-1).
 7. The aromatic amine compoundaccording to claim 2, wherein the aromatic amine compound is representedby the formula (5) in which two of the Ar² to Ar⁴ are each representedby the formula (1-2), and one of the Ar² to Ar⁴ represents a substitutedor unsubstituted aryl group having 6 to 16 ring carbon atoms.
 8. Thearomatic amine compound according to claim 2, wherein the aromatic aminecompound is represented by the formula (5) in which two of the Ar² toAr⁴ are each represented by the formula (1-1), and one of the Ar² to Ar⁴represents a substituted or unsubstituted aryl group having 6 to 16 ringcarbon atoms.
 9. The aromatic amine compound according to claim 2,wherein the aromatic amine compound is represented by the formula (5) inwhich at least one of the Ar² to Ar⁴ is represented by the formula(1-2), and at least one of the Ar² to Ar⁴ is represented by the formula(1-1).
 10. The aromatic amine compound according to claim 2, wherein thearomatic amine compound is represented by the formula (5) in which theAr² is represented by the formula (1-2), and the Ar³ and the Ar⁴ areeach independently represented by the formula (1-1).
 11. The aromaticamine compound according to claim 2, wherein the aromatic amine compoundis represented by the formula (5) in which the Ar² and the Ar³ are eachrepresented by the formula (1-3), and the Ar⁴ is represented by thegeneral formula (1-1).
 12. The aromatic amine compound according toclaim 1, wherein the compound has a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms which is a terphenyl group. 13.The aromatic amine compound according to claim 1, wherein the aromaticamine compound is represented by the formula (5).
 14. A material for anorganic electroluminescence device comprising the aromatic aminecompound according to claim
 1. 15. A hole transporting material for anorganic electroluminescence device comprising the aromatic aminecompound according to claim
 1. 16. An organic electroluminescencedevice, comprising an organic thin film layer formed of one or morelayers including at least a light emitting layer, the organic thin filmlayer being interposed between a cathode and an anode, wherein at leastone layer of the organic thin film layer comprises the aromatic aminecompound according to claim
 1. 17. The organic electroluminescencedevice according to claim 16, wherein: the organic thin film layer has ahole transporting layer and/or a hole injecting layer; and the aromaticamine compound is incorporated into the hole transporting layer and/orthe hole injecting layer.
 18. The organic electroluminescence deviceaccording to claim 16, wherein: the organic thin film layer has a holetransporting zone including at least a hole transporting layer and ahole injecting layer; and the aromatic amine compound is incorporatedinto a layer out of direct contact with the light emitting layer in thehole transporting zone.
 19. The organic electroluminescence deviceaccording to claim 16, wherein the light emitting layer comprises astyrylamine compound and/or an arylamine compound.
 20. The organicelectroluminescence device according to claim 16, wherein a layer incontact with the anode, which is a layer for forming a hole injectinglayer and/or a hole transporting layer, comprises a layer containing anacceptor material.
 21. The organic electroluminescence device accordingto claim 16, wherein the organic electroluminescence device emits bluelight.
 22. The aromatic amine compound according to claim 1, wherein L¹and L⁴ to L¹² each independently represent a phenylene group, anaphthylene group, a biphenylene group, a terphenylene group, afluorenylene group or a 9,9-dimethylfluorenylene group.
 23. The aromaticamine compound according claim 1, wherein the L¹ and L⁴ to L¹² are eachindependently represented by any one of the following formulae (4),(10), and (11):

where: R⁷ to R¹¹ each independently represent a linear or branched alkylgroup having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, atriarylsilyl group having 18 to 30 ring carbon atoms, an alkylarylsilylgroup having 8 to 15 carbon atoms whose aryl portion has 6 to 14 ringcarbon atoms, an aryl group having 6 to 14 ring carbon atoms, a halogenatom, or a cyano group, and a plurality of R⁷'s to R¹¹'s adjacent toeach other may be bonded to each other to form a saturated orunsaturated ring; R¹² and R¹³ each independently represent a linear orbranched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl grouphaving 3 to 10 ring carbon atoms; g, h, and i each independentlyrepresent an integer of 0 to 4; and j and k each independently representan integer of 0 to
 3. 24. The aromatic amine compound according to claim1, wherein the aryl group having 6 to 50 ring carbon atoms represents aphenyl group, a naphthyl group, a biphenyl group, a terphenyl group or afluorenyl group.